Skip to content
Licensed Unlicensed Requires Authentication Published by De Gruyter September 14, 2018

Recent advances in the application of carbohydrates as renewable feedstocks for the synthesis of nitrogen-containing compounds

  • S. Iraj Sadraei , Brent St Onge and John F. Trant EMAIL logo
From the journal Physical Sciences Reviews

Abstract

Carbohydrates, in the form of chitin, chitosan and cellulose, are one of the most available, renewable, and sustainable chemical feedstocks. Their conversion to biofuels, fine chemicals, and industrially-relevant monomers is becoming increasingly viable and promising as innovation decreases the price of this technology, and climate change and the price of fossil fuels increases the social and economic costs of using traditional feedstocks. In recent years, carbohydrates have been increasingly used as sources for nitrogen-containing fine chemicals. This chapter, with 86 references, provides a brief overview of the conversion of carbohydrate biomass to the standard hydrocarbon and oxygen-containing derivatives, and then provides a survey of recent progress in converting the biopolymers, and the derived mono and di-saccharides, into nitrogen-containing molecules with a special focus on N-heterocycle synthesis for medicinal applications.

Abbreviations

3A5AF

3-acetamido-5-acetylfuran

AgOTf

Silver Triflate

Cu(OTf)2

Copper triflate

DCE

1,2-dichloroethane

DCM

Dichloromethane

DFA

di-d-fructose dianhydrides

DMA

Dimethylacetamide

DMF

Dimethylformamide

DMSO

Dimethyl sulfoxide

dtbpy

4,4’-di tert butyl-2,2’-bipyridine

EG

Ethylene glycol

Fruf

Fructofuranosyl

Gal

Galactose

GC-MS

Gas chromatography–mass spectrometry

GPC

Gel permeation chromatography

GlcNAc

N-acetyl-2-deoxy-2-amino-d-glucose

Glcp

Glucopyranosyl

α-Gls

α-glucosidase

Gly

Glycerine

5-HMF

5-(hydroxymethyl)furfural

LA

Levulinic acid

LC-MS

Liquid Chromatography-Mass Spectrometry

2-MP

2-methyl pyrazine

Ms

Mesyl

MsCl

Mesyl Chloride

NAG

N-acetyl-2-deoxy-2-amino-d-glucose

NMP

N-methyl-2-pyrrolidone

PFH’s

Pyrimidine-fused Heterocycles

PHPFH

Polyhydroxylated pyrimidine-fused heterocycles

PTSA

p-toluenesulfonic acid

Pyr

Pyridine

RT

Room temperature

THF

Tetrahydrofuran

TMSOTf

Trimethylsilyl Trifluoromethanesulfonate

Tf2O

Trifluoromethanesulfonic Anhydride

USD

United States Dollar

Acknowledgements

The authors would like to thank the University of Windsor for supporting the writing of this Chapter through Start-Up Funds to JFT. BSO would like to thank his supervisor, Prof. J. Green, for his support during the writing process.

References

[1] Jiménez-González C, Poechlauer P, Broxterman QB, Yang BS, am Ende D, Baird J et al. Key green engineering research areas for sustainable manufacturing: a perspective from pharmaceutical and fine chemicals manufacturers. Org Proc Res Dev. 2011;15:900–1110.1021/op100327dSearch in Google Scholar

[2] Priddy RD. Sustainability: the train has left the station. MRS Energy Sustainability. 2017;4:E3.10.1557/mre.2017.4Search in Google Scholar

[3] Krane J. Climate change and fossil fuel: an examination of risks for the energy industry and producer states. MRS Energy Sustainability. 2017;4:E2.10.1557/mre.2017.3Search in Google Scholar

[4] Sheldon RA. Green chemistry and resource efficiency: towards a green economy. Green Chem. 2016;18:3180–3.10.1039/C6GC90040BSearch in Google Scholar

[5] Colmenares JC. Nanophotocatalysis in selective transformations of lignocellulose-derived molecules: a green approach for the synthesis of fuels, fine chemicals, and pharmaceuticals. RSC Green Chem Ser. 2016;42:168–201.10.1039/9781782622642-00168Search in Google Scholar

[6] Gandini A. Furans as offspring of sugars and polysaccharides and progenitors of a family of remarkable polymers: a review of recent progress. Polym Chem. 2010;1:245–51.10.1039/B9PY00233BSearch in Google Scholar

[7] Galbis JA, García-Martín MG. Synthetic polymers from readily available monosaccharides. In: Rauter AP, Vogel P, Queneau Y, editors. Carbohydrates in sustainable development II. Berlin, Heidelberg: Springer Berlin Heidelberg, 2010:147–76.10.1007/128_2010_57Search in Google Scholar PubMed

[8] El Kadib A. Chitosan as a sustainable organocatalyst: a concise overview. ChemSusChem. 2015;8:217–44.10.1002/cssc.201402718Search in Google Scholar PubMed

[9] Lichtenthaler FW, Mondel S. Perspectives in the use of low molecular weight carbohydrates as organic raw materials. Pure Appl Chem. 1997;69:1853–66.10.1351/pac199769091853Search in Google Scholar

[10] Mika LT, Cséfalvay E, Németh Á. Catalytic conversion of carbohydrates to initial platform chemicals: chemistry and sustainability. Chem Rev. 2018;118:505–613.10.1021/acs.chemrev.7b00395Search in Google Scholar PubMed

[11] Khoo HH, Ee WL, Isoni V. Bio-chemicals from lignocellulose feedstock: sustainability, LCA and the green conundrum. Green Chem. 2016;18:1912–22.10.1039/C5GC02065DSearch in Google Scholar

[12] Roy Goswami S, Dumont M-J, Raghavan V. Starch to value added biochemicals. Starch/Staerke. 2016;68:274–86.10.1002/star.201500058Search in Google Scholar

[13] Isikgor FH, Becer CR. Lignocellulosic biomass: a sustainable platform for the production of bio-based chemicals and polymers. Polym Chem. 2015;6:4497–559.10.1039/C5PY00263JSearch in Google Scholar

[14] Holmberg AL, Reno KH, Wool RP, Epps IIITH. Biobased building blocks for the rational design of renewable block polymers. Soft Matter. 2014;10:7405–24.10.1039/C4SM01220HSearch in Google Scholar PubMed

[15] Lichtenthaler FW, Peters S. Carbohydrates as green raw materials for the chemical industry. C R Chim. 2004;7:65–90.10.1016/j.crci.2004.02.002Search in Google Scholar

[16] Sheldon RA. Green and sustainable manufacture of chemicals from biomass: state of the art. Green Chem. 2014;16:950–63.10.1039/C3GC41935ESearch in Google Scholar

[17] Climent MJ, Corma A, Iborra S. Conversion of biomass platform molecules into fuel additives and liquid hydrocarbon fuels. Green Chem. 2014;16:516–47.10.1039/c3gc41492bSearch in Google Scholar

[18] Yan L, Yao Q, Fu Y. Conversion of levulinic acid and alkyl levulinates into biofuels and high-value chemicals. Green Chem. 2017;19:5527–47.10.1039/C7GC02503CSearch in Google Scholar

[19] Gao X, Chen X, Zhang J, Guo W, Jin F, Yan N. Transformation of chitin and waste shrimp shells into acetic acid and pyrrole. ACS Sustainable Chem Eng. 2016;4:3912–20.10.1021/acssuschemeng.6b00767Search in Google Scholar

[20] Jin F, Zhou Z, Moriya T, Kishida H, Higashijima H, Enomoto H. Controlling hydrothermal reaction pathways to improve acetic acid production from carbohydrate biomass. Environ Sci Technol. 2005;39:1893–902.10.1021/es048867aSearch in Google Scholar PubMed

[21] Liguori F, Moreno-Marrodan C, Barbaro P. Environmentally friendly synthesis of γ-valerolactone by direct catalytic conversion of renewable sources. ACS Catalysis. 2015;5:1882–94.10.1021/cs501922eSearch in Google Scholar

[22] Szabolcs A, Molnar M, Dibo G, Mika LT. Microwave-assisted conversion of carbohydrates to levulinic acid: an essential step in biomass conversion. Green Chem. 2013;15:439–45.10.1039/C2GC36682GSearch in Google Scholar

[23] Bozell JJ, Moens L, Elliott DC, Wang Y, Neuenscwander GG, Fitzpatrick SW et al. Production of levulinic acid and use as a platform chemical for derived products. Resour, Conserv Recycl. 2000;28:227–3910.1016/S0921-3449(99)00047-6Search in Google Scholar

[24] Werpy T, Petersen G Top Value Added Chemicals from Biomass: Volume I – Results of Screening for Potential Candidates from Sugars and Synthesis Gas: National Renewable Energy Lab., Golden, CO (US); 2004. Report No.: DOE/GO-102004-1992; TRN: US200427 United States.10.2172/15008859Search in Google Scholar

[25] Lee AF. Catalysing sustainable fuel and chemical synthesis. Appl Petrochem Res. 2014;4:11–31.10.1201/b18526-3Search in Google Scholar

[26] Kan T, Strezov V, Evans TJ. Lignocellulosic biomass pyrolysis: A review of product properties and effects of pyrolysis parameters. Renewable Sustainable Energy Rev. 2016;57:1126–40.10.1016/j.rser.2015.12.185Search in Google Scholar

[27] Bond JQ, Upadhye AA, Olcay H, Tompsett GA, Jae J, Xing R et al. Production of renewable jet fuel range alkanes and commodity chemicals from integrated catalytic processing of biomass. Energy Environ Sci. 2014;7:1500–2310.1039/C3EE43846ESearch in Google Scholar

[28] Beerthuis R, Rothenberg G, Shiju NR. Catalytic routes towards acrylic acid, adipic acid and ?-caprolactam starting from biorenewables. Green Chem. 2015;17:1341–61.10.1039/C4GC02076FSearch in Google Scholar

[29] Chatzidimitriou A, Bond JQ. Oxidation of levulinic acid for the production of maleic anhydride: breathing new life into biochemicals. Green Chem. 2015;17:4367–76.10.1039/C5GC01000DSearch in Google Scholar

[30] Chen W-H, Lin B-J, Huang M-Y, Chang J-S. Thermochemical conversion of microalgal biomass into biofuels: A review. Bioresour Technol. 2015;184:314–27.10.1016/j.biortech.2014.11.050Search in Google Scholar PubMed

[31] Bicker M, Hirth J, Vogel H. Dehydration of fructose to 5-hydroxymethylfurfural in sub- and supercritical acetone. Green Chem. 2003;5:280–4.10.1039/b211468bSearch in Google Scholar

[32] Caes BR, Teixeira RE, Knapp KG, Raines RT. Biomass to furanics: renewable routes to chemicals and fuels. ACS Sustainable Chem Eng. 2015;3:2591–605.10.1021/acssuschemeng.5b00473Search in Google Scholar

[33] Huang H, Denard CA, Alamillo R, Crisci AJ, Miao Y, Dumesic JA et al. Tandem catalytic conversion of Glucose to 5-Hydroxymethylfurfural with an immobilized Enzyme and a solid acid. ACS Catalysis. 2014;4:2165–810.1021/cs500591fSearch in Google Scholar

[34] Luterbacher JS, Rand JM, Alonso DM, Han J, Youngquist JT, Maravelias CT et al. Nonenzymatic sugar production from biomass using biomass-derived γ-valerolactone. Science. 2014;343:277–8010.1126/science.1246748Search in Google Scholar

[35] Chuntanapum A, Matsumura Y. Formation of tarry material from 5-HMF in subcritical and supercritical water. Ind Eng Chem Res. 2009;48:9837–46.10.1021/ie900423gSearch in Google Scholar

[36] Akien GR, Qi L, Horvath IT. Molecular mapping of the acid catalysed dehydration of fructose. Chem Commun. 2012;48:5850–2.10.1039/c2cc31689gSearch in Google Scholar

[37] Antal MJ, Mok WSL, Richards GN. Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose. Carbohydr Res. 1990;199:91–109.10.1016/0008-6215(90)84096-DSearch in Google Scholar

[38] Amarasekara AS, Williams LD, Ebede CC. Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study. Carbohydr Res. 2008;343:3021–4.10.1016/j.carres.2008.09.008Search in Google Scholar PubMed PubMed Central

[39] Omari KW, Besaw JE, Kerton FM. Hydrolysis of chitosan to yield levulinic acid and 5-hydroxymethylfurfural in water under microwave irradiation. Green Chem. 2012;14:1480–7.10.1039/c2gc35048cSearch in Google Scholar

[40] Andrić P, Meyer AS, Jensen PA, Dam-Johansen K. Reactor design for minimizing product inhibition during enzymatic lignocellulose hydrolysis: I. Significance and mechanism of cellobiose and glucose inhibition on cellulolytic enzymes. Biotechnol Adv. 2010;28:308–24.10.1016/j.biotechadv.2010.01.003Search in Google Scholar PubMed

[41] Mascal M, Nikitin EB. Dramatic advancements in the saccharide to 5-(Chloromethyl)furfural conversion reaction. ChemSusChem. 2009;2:859–61.10.1002/cssc.200900136Search in Google Scholar

[42] Ruppel JV, Snyder NL, Thompson AD, Farnsworth TW. Furans, benzofurans, thiophenes, and benzothiophenes. In: Li JJ, editor. Heterocyclic chemistry in drug discovery. Hoboken, N.J.: John Wiley & Sons, Inc., 2013:119–96.Search in Google Scholar

[43] Sperry JB, Wright DL. Furans, thiophenes and related heterocycles in drug discovery. Curr Opin Drug Discovery Dev. 2005;8:723–40.10.1002/chin.200615242Search in Google Scholar

[44] Kerton FM, Marriot R. Chapter 7 room-temperature ionic liquids and eutectic mixtures. In: Alternative solvents for green chemistry. 2nd ed. London: The Royal Society of Chemistry, 2013:175–209.Search in Google Scholar

[45] El Seoud OA, Koschella A, Fidale LC, Dorn S, Heinze T. Applications of ionic liquids in Carbohydrate chemistry: a window of opportunities. Biomacromolecules. 2007;8:2629–47.10.1021/bm070062iSearch in Google Scholar

[46] Benedetto A, Ballone P. Room temperature ionic liquids meet biomolecules: a microscopic view of structure and dynamics. ACS Sustainable Chem Eng. 2016;4:392–412.10.1021/acssuschemeng.5b01385Search in Google Scholar

[47] Buntara T, Noel S, Phua PH, Melián-Cabrera I, De Vries JG, Heeres HJ. Caprolactam from renewable resources: catalytic conversion of 5-Hydroxymethylfurfural into Caprolactone. Angew Chem Int Ed. 2011;50:7083–7.10.1002/anie.201102156Search in Google Scholar

[48] Drover MW, Omari KW, Murphy JN, Kerton FM. Formation of a renewable amide, 3-acetamido-5-acetylfuran, via direct conversion of N-acetyl-d-glucosamine. RSC Adv. 2012;2:4642–4.10.1039/c2ra20578eSearch in Google Scholar

[49] Franich RA, Goodin SJ, Wilkins AL. Acetamidofurans, acetamidopyrones, and acetamidoacetaldehyde from pyrolysis of chitin and n-acetylglucosamine. J Anal Appl Pyrolysis. 1984;7:91–100.10.1016/0165-2370(84)80043-1Search in Google Scholar

[50] Chen J, Wang M, Ho C-T. Volatile compounds generated from thermal degradation of N-acetylglucosamine. J Agric Food Chem. 1998;46:3207–9.10.1021/jf980129gSearch in Google Scholar

[51] Chen X, Chew SL, Kerton FM, Yan N. Direct conversion of chitin into a N-containing furan derivative. Green Chem. 2014;16:2204–12.10.1039/C3GC42436GSearch in Google Scholar

[52] Einbu A, Varum KM. Characterization of Chitin and its Hydrolysis to GlcNAc and GlcN. Biomacromolecules. 2008;9:1870–5.10.1021/bm8001123Search in Google Scholar PubMed

[53] Vaaje-Kolstad G, Westereng B, Horn SJ, Liu Z, Zhai H, Sorlie M et al. An Oxidative Enzyme boosting the enzymatic conversion of recalcitrant polysaccharides. Science. 2010;330:219–2210.1126/science.1192231Search in Google Scholar PubMed

[54] Streith J, Boiron A, Frankowski A, Le Nouen D, Rudyk H, Tschamber T. On the way to glycoprocessing inhibitors: a general one-pot synthesis of Imidazolosugars. Synthesis. 1995;1995:944–6.10.1055/s-1995-4040Search in Google Scholar

[55] Brust A, Cuny E. Conversion of reducing carbohydrates into hydrophilic substituted imidazoles. Green Chem. 2013;15:2993–98.10.1039/c3gc41203bSearch in Google Scholar

[56] Wrodnigg TM, Kartusch C, Illaszewicz C. The amadori rearrangement as key reaction for the synthesis of neoglycoconjugates. Carbohydr Res. 2008;343:2057–66.10.1016/j.carres.2008.02.022Search in Google Scholar PubMed

[57] Brust A, Cuny E. Reducing disaccharides and their 1,2-dicarbonyl intermediates as building blocks for nitrogen heterocycles. RSC Adv. 2014;4:5759–67.10.1039/c3ra47349jSearch in Google Scholar

[58] Mohana Roopan S, Sompalle R. Synthetic chemistry of pyrimidines and fused pyrimidines: a review. Synth Commun. 2016;46:645–72.10.1080/00397911.2016.1165254Search in Google Scholar

[59] Gaurav J, Himanshu N, Jimi Marin A, Gajendra SV, Sunil M, Raj K. Pyrimidine-fused derivatives: synthetic strategies and medicinal attributes. Curr Top Med Chem ((Sharjah, United Arab Emirates)). 2016;16: 3175–210.10.2174/1568026616666160506145046Search in Google Scholar PubMed

[60] Schenone S, Radi M, Musumeci F, Brullo C, Botta M. Biologically driven synthesis of Pyrazolo[3,4-d]pyrimidines as protein kinase inhibitors: an old scaffold as a new tool for medicinal chemistry and chemical biology studies. Chem Rev. 2014;114:7189–238.10.1021/cr400270zSearch in Google Scholar PubMed

[61] Bahashwan SA. Pharmacological studies of some pyrimidino derivatives. Afr J Pharm Pharmacol. 2011;5:527–31.10.5897/AJPP11.094Search in Google Scholar

[62] Singh B, Maheshwari A, Dak G, Sharma K, Talesara GL. Studies of antimicrobial activities of some 4-Thiazolidinone Fused pyrimidines, [1,5]-Benzodiazepines and their Oxygen substituted Hydroxylamine derivatives. Indian J Pharm Sci. 2010;72:607–12.10.4103/0250-474X.78529Search in Google Scholar PubMed PubMed Central

[63] Mah R. Pyrimidine-based kinase inhibitors in cancer chemotherapy. In: Dinges J, Lamberth C, editors. Bioactive heterocyclic compound classes. Weinheim, Germany: Wiley-VCH Verlag GmbH & Co. KGaA, 2012:257–71.10.1002/9783527664450.ch16Search in Google Scholar

[64] Banday AH, Mir BP, Lone IH, Suri KA, Kumar HMS. Studies on novel D-ring substituted steroidal pyrazolines as potential anticancer agents. Steroids. 2010;75:805–09.10.1016/j.steroids.2010.02.014Search in Google Scholar PubMed

[65] Shamroukh AH, Zaki MEA, Morsy EMH, Abdel-Motti FM, Abdel-Megeid FME. Synthesis of Pyrazolo[4′,3′:5,6]pyrano[2,3-d]pyrimidine derivatives for antiviral evaluation. Arch Pharm. 2007;340:236–43.10.1002/ardp.200700005Search in Google Scholar PubMed

[66] Amir M, Javed SA, Kumar H. Pyrimidine as antiinflammatory agent: a review. Indian J Pharm Sci. 2007;69:337–43.10.4103/0250-474X.34540Search in Google Scholar

[67] Yousefi R, M-M A-M, Mokhtari F, Panahi F, Mehraban MH, Khalafi-Nezhad A. Pyrimidine-fused heterocycle derivatives as a novel class of inhibitors for α-glucosidase. J Enzyme Inhib Med Chem. 2013;28:1228–35.10.3109/14756366.2012.727812Search in Google Scholar PubMed

[68] Nourisefat M, Panahi F, Khalafi-Nezhad A. Carbohydrates as a reagent in multicomponent reactions: one-pot access to a new library of hydrophilic substituted pyrimidine-fused heterocycles. Org Biomol Chem. 2014;12:9419–26.10.1039/C4OB01791ASearch in Google Scholar PubMed

[69] Wang J, Xi J, Wang Y. Recent advances in the catalytic production of glucose from lignocellulosic biomass. Green Chem. 2015;17:737–51.10.1039/C4GC02034KSearch in Google Scholar

[70] Lahiri R, Ansari AA, Vankar YD. Recent developments in design and synthesis of bicyclic azasugars, carbasugars and related molecules as glycosidase inhibitors. Chem Soc Rev. 2013;42:5102–18.10.1039/c3cs35525jSearch in Google Scholar PubMed

[71] Robertson J, Stevens K. Pyrrolizidine alkaloids: occurrence, biology, and chemical synthesis. Nat Prod Rep. 2017;34:62–89.10.1039/C5NP00076ASearch in Google Scholar

[72] Dharuman S, Gupta P, Kancharla PK, Vankar YD. Synthesis of 2-Nitroglycals from Glycals using the Tetrabutylammonium Nitrate–trifluoroacetic Anhydride–triethylamine reagent system and base-catalyzed ferrier rearrangement of Acetylated 2-Nitroglycals. J Org Chem. 2013;78:8442–50.10.1021/jo401165ySearch in Google Scholar PubMed

[73] Ritthiwigrom T, Au CWG, Pyne SG. Structure, biological activities, and synthesis of hyacinthacine alkaloids and their stereoisomers. Curr Org Synth. 2012;9:583–612.10.2174/157017912803251765Search in Google Scholar

[74] Murali R, Ramana CV, Nagarajan M. Synthesis of 1,2-cyclopropanated sugars from glycals. J Chem Soc Chem Commun. 1995;1995:217–8.10.1039/c39950000217Search in Google Scholar

[75] Reissig H-U ZR. Donor-acceptor-substituted Cyclopropane derivatives and their application in organic synthesis. Chem Rev (Washington, DC, U S). 2003;103:1151–96.10.1021/cr010016nSearch in Google Scholar PubMed

[76] Wurz RP, Charette AB. Doubly activated cyclopropanes as synthetic precursors for the preparation of 4-nitro- and 4-cyano-dihydropyrroles and pyrroles. Org Lett. 2005;7:2313–6.10.1021/ol050442lSearch in Google Scholar PubMed

[77] Shen X, Xia J, Liang P, Ma X, Jiao W, Shao H. Zn(OTf)2 promoted rearrangement of 1,2-cyclopropanated sugars with amines: a convenient method for the synthesis of 3-polyhydroxyalkyl-substituted pyrrole derivatives. Org Biomol Chem. 2015;13:10865–73.10.1039/C5OB01620GSearch in Google Scholar

[78] Masuda H, Mihara S. Olfactive properties of alkylpyrazines and 3-substituted 2-alkylpyrazines. J Agric Food Chem. 1988;36:584–7.10.1021/jf00081a044Search in Google Scholar

[79] Miniyar PB, Murumkar PR, Patil PS, Barmade MA, Bothara KG. Unequivocal role of Pyrazine ring in medicinally important compounds: a review. Mini-Rev Med Chem. 2013;13:1607–25.10.2174/1389557511313110007Search in Google Scholar PubMed

[80] Ferreira SB, Kaiser CR. Pyrazine derivatives: a patent review (2008 – present). Expert Opin Ther Pat. 2012;22:1033–51.10.1517/13543776.2012.714370Search in Google Scholar PubMed

[81] Fors SM, Olofsson BK. Alkylpyrazines, volatiles formed in the maillard reaction. i. determination of odour detection thresholds and odour intensity functions by dynamic olfactometry. Chem Senses. 1985;10:287–96.10.1093/chemse/10.3.287Search in Google Scholar

[82] Wang A, Zhang T. One-pot conversion of cellulose to ethylene glycol with multifunctional tungsten-based catalysts. Acc Chem Res. 2013;46:1377–86.10.1021/ar3002156Search in Google Scholar PubMed

[83] Ara KM, Taylor LT, Ashraf-Khorassani M, Coleman WM. Alkyl pyrazine synthesis via an open heated bath with variable sugars, ammonia, and various amino acids. J Sci Food Agric. 2017;97:2263–70.10.1002/jsfa.8039Search in Google Scholar PubMed

[84] Horne G, Wilson FX, Tinsley J, Williams DH, Storer R. Iminosugars past, present and future: medicines for tomorrow. Drug Discovery Today. 2011;16:107–18.10.1016/j.drudis.2010.08.017Search in Google Scholar PubMed

[85] Asano N. Azaglycomimetics: natural occurrence, biological activity, and application. In: Fraser-Reid B, Tatsuta K, Thiem J, editors. Glycoscience. 2nd ed. Berlin: Springer-Verlag, 2008:1887–911.10.1007/978-3-540-30429-6_48Search in Google Scholar

[86] Naresh A, Marumudi K, Kunwar AC, Rao BV. Palladium-catalyzed double allylation of sugar-imines by employing tamaru-kimura’s protocol: access to unnatural iminosugars. Org Lett. 2017;19:1642–5.10.1021/acs.orglett.7b00441Search in Google Scholar PubMed

Published Online: 2018-09-14

© 2019 Walter de Gruyter GmbH, Berlin/Boston

Downloaded on 21.5.2024 from https://www.degruyter.com/document/doi/10.1515/psr-2018-0074/html
Scroll to top button