Abstract
This chapter summarizes the concepts and chemistry developed by Ley’s group in relation to the relevance of reactivity tuning in oligosaccharide coupling reactions. The recognition that protecting groups affect the reactivity of glycosyl donors allowed Ley’s group to make imaginative use of their 1,2-diacetal protecting groups. The combination of 1,2-diacetals with the presence of different anomeric leaving groups provides up to four different levels of reactivity. The exploitation of these reactivity levels in chemoselective glycosylation processes (reactivity tuning) has allowed the development of highly simplified routes to several complex oligosaccharides in step-wise or one-pot procedures.
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Abbreviations
- Aloc:
-
Allyloxycarbonyl
- BDA:
-
Butane-2,3-diacetals
- bis-DHP:
-
3.3′,4.4′-Tetrahydro-6,6′-bis-2H-pyran
- Bn:
-
Benzyl (CH2Ph)
- Boc:
-
tert-Butoxycarbonyl
- Bz:
-
Benzoyl
- Cbz:
-
Benzyloxycarbonyl
- CDA:
-
Cyclohexane-1,2-diacetals
- CSA:
-
Camphorsulfonic acid
- DF:
-
Deactivation factor
- Dispoke:
-
Dispiroketal
- FBn:
-
p-Fluorobenzyl
- gp:
-
Glycoprotein
- GPI:
-
Glycosylphosphatidylinositol
- HIV:
-
Human immunodeficiency virus
- HPLC:
-
High pressure liquid chromatography
- IDCP:
-
Iodonium dicollidine perchlorate
- NIS:
-
N-Iodosuccinimide
- RRV:
-
Relative reactivity values
- SN2:
-
Bimolecular nucleophilic substitution
- TBAF:
-
Tetra-n-butyl ammonium fluoride
- TBDPS:
-
tert-Butyldiphenylsilyl
- TBS:
-
tert-Butyldimethylsilyl
- TESOTf:
-
Triethylsilyltrifluoromethanesulfonate
- TFA:
-
Trifluoromethanesulfonic acid
- TfOH:
-
Triflic acid
- TMB:
-
2,2,3,3-Tetramethoxybutane
- TMC:
-
1,1,2,2-Tetramethoxycyclohexane
References
Vliegenhart JFG, Doorland L, Van Halbeek H (1983) Adv Carbohydr Chem Biochem 41:209
Dell A (1987) Adv Carbohydr Chem Biochem 45:21
Varki A (1993) Glycobiology 3:97
Sharon N, Lis H (1993) Sci Am 268:82
Montreuil J (1980) Adv Carbohydr Chem Biochem 37:157
Kobata A (1984) In: Ginsberg V, Robbins PW (eds) Biology of carbohydrates. Wiley, New York, p 87
Gottschalk A (ed) (1972) Glycoproteins. Elsevier, Amsterdam
Sharon N, Lis H (1991) Eur J Biochem 1:218
Lis H, Sharon N (1998) Chem Rev 98:637
Sharon N, Lis H (1981) Chem Eng News 59:21
Karlsson K-A (1991) Trends Pharmacol Sci 12:265
Karlsson KA (1989) Annu Rev Biochem 58:309
Rademacher TW, Parekh RB, Dwek RA (1988) Annu Rev Biochem 57:785
Goldstein EJ (1979) Carbohydrate protein interaction. ACS Symp Series, vol 88. American Chemical Society, Washington, DC
Feizi T (1985) Nature 314:53
Feizi T, Childs RA (1987) Biochem J 245:1
Kocienski PJ (2005) Protecting groups, 3rd edn. Georg Thieme, Stuttgart
Robertson J (2000) Protecting group chemistry. Oxford University Press, New York
Greene TWP, Wuts GM (1999) Protective groups in organic synthesis, 3rd edn. Wiley, New York
Hanson JR (1999) Protecting groups in organic synthesis. Sheffield Academic Press, New York
Ley SV, Downham R, Edwards PJ, Innes JE, Woods M (1995) Contemp Org Synth 2:365
Ley SV, Baeschlin DK, Dixon DJ, Foster AC, Ince SJ, Priepke HWM, Reynolds DJ (2001) Chem Rev 101:53
Ley SV, Polara A (2007) J Org Chem 72:5943
van Boeckel CAA, van Boom JH (1985) Tetrahedron 41:4567
Ziegler T (1994) Angew Chem Int Ed Eng 33:22
Ley SV, Woods M, Zanotti-Gerosa A (1992) Synthesis:52
Hughes AB, Ley SV, Priepke HWM, Woods M (1994) Tetrahedron Lett 35:773
Ley SV, Priepke HWM, Warriner SL (1994) Angew Chem Int Ed Engl 33:2290
Lemieux RU (1971) Pure Appl Chem 25:527
Juaristi E, Cuevas G (1992) Tetrahedron 48:5019
Entwistle DA, Hughes AB, Ley SV, Visentin G (1994) Tetrahedron Lett 33:777
Edwards PJ, Entwistle DA, Genicot C, Ley SV, Visentin G (1994) Tetrahedron Asymmetry 5:2609
Montchamp JL, Tian F, Hart ME, Frost JW (1996) J Org Chem 61:3897
Douglas NL, Ley SV, Osborn HMI, Owen DR, Priepke HWM, Warriner SL (1996) Synlett:793
Hense A, Ley SV, Osborn HMI, Owen DR, Poisson JF, Warriner SL, Wesson KE (1997) J Chem Soc Perkin Trans I:2023
Grice P, Ley SV, Pietruszka J, Priepke HWM, Warriner SL (1997) J Chem Soc Perkin Trans I:351
Paulsen H, Richter A, Sinnwell V, Stenzel W (1974) Carbohydr Res 38:312
Paulsen H (1982) Angew Chem Int Ed Engl 21:155
Mootoo DR, Konradsson P, Udodong U, Fraser-Reid B (1988) J Am Chem Soc 110:5583
Fraser-Reid B, Udodong U, Wu ZF, Ottosson H, Merritt JR, Rao CS, Roberts C, Madsen R (1992) Synlett: 927 and references therein
Veeneman GH, van Boom JH (1990) Tetrahedron Lett 31:275
Friesen RW, Danishefsky SJ (1989) J Am Chem Soc 111:6656
Barrena MI, Echarri R, Castillón S (1996) Synlett:675
Baeschlin DK, Chaperon AR, Charbonneau V, Green LG, Ley SV, Lucking U, Walther E (1998) Angew Chem Int Ed 37:3423
Hashimoto SI, Sakamoto H, Honda T, Abe H, Nakamura SI, Ikegami S (1997) Tetrahedron Lett 38:8969
Chiba H, Funasaka S, Kiyota K, Mukaiyama T (2002) Chem Lett:746
Kamat MN, Demchenko AV (2005) Org Lett 7:3215
Smoot JT, Pornsuriyasak P, Demchenko AV (2005) Angew Chem Int Ed 44:7123
Mydock LK, Demchenko AV (2008) Org Lett 10:2103
Mydock LK, Demchenko AV (2008) Org Lett 10:2107
Parameswar KT, AR DAV (2010) Org Lett 12:3078
Pedersen CM, Nordstrom LU, Bols M (2007) J Am Chem Soc 129:9222
Jensen HH, Pedersen CM, Bols M (2007) Chem Eur J 13:7576
Douglas NL, Ley SV, Lücking U, Warriner SL (1999) J Chem Soc Perkin Trans I:51
Green LG, Ley SV (2000) In: Ernst B, Hart GW, Sinaÿ P (eds) Carbohydrates in chemistry and biology. Wiley-VCH, Weinheim, p 427
Zhang Z, Ollmann IR, Ye XS, Wischnat R, Baasov T, Wong CH (1999) J Am Chem Soc 121:734
Lee J-C, Greenberg WA, Wong CH (2006) Nat Protoc 1:3143
Lahmann M, Oscarson S (2002) Can J Chem 80:889
Pedersen CM, Marinescu LG, Bols M (2008) Chem Commun:2645
Li X, Huang L, Hu X, Huang X (2009) Org Biomol Chem 7:117
Fraser-Reid B, Wu Z, Andrews CW, Skowronski E, Bowen JP (1991) J Am Chem Soc 113:1434
Andrews CW, Rodebaugh R, Fraser-Reid B (1996) J Org Chem 61:5280
Jensen HH, Nordstrom LU, Bols M (2004) J Am Chem Soc 126:9205
Boons G-J, Grice P, Leslie R, Ley SV, Yeung LL (1993) Tetrahedron Lett 34:8523
Wang Y, Ye XS, Zhang LH (2007) Org Biomol Chem 5:2189
Ley SV, Priepke HWM (1994) Angew Chem Int Ed Engl 33:2292
Grice P, Ley SV, Pietruszka J, Priepke HWM, Walther EPE (1995) Synlett:781
Lis H, Sharon N (1978) J Biol Chem 253:3468
Li E, Kornfeld S (1979) J Biol Chem 254:1600
Dorland L, van Halbeek H, Vliegenthart JFG, Lis H, Sharon N (1981) J Biol Chem 256:7708
Mizuochi T, Spellman MW, Larkin M, Solomon J, Basa LJ, FeiLi T (1988) Biochem J 254:599
Doores KJ, Bonomelli C, Harvey DJ, Vasiljevic S, Dwek RA, Burton DR, Crispin M, Scanlan CN (2010) Proc Natl Acad Sci USA 107:13800
Scanlan CS, Offer J, Zitzmann N, Dwek RA (2007) Nature 446:1038
Krauss IJ, Joyce JG, Finnefrock AC, Song HC, Dudkin VY, Geng X, Warren JD, Chastain M, Shiver JW, Danishefsky S (2007) J Am Chem Soc 129:11042
Sanders RW, Venturi M, Schiffner L, Kalyanaraman R, Katinger H, Lloyd KO, Kwong PD, Moore JP (2002) J Virol 76:7293
Calarese DA, Scanlan CN, Zwick MB, Deechongkit S, Mimura Y, Kunert R, Zhu P, Wormald MR, Stanfield RL, Roux KH, Kelly JW, Rudd PM, Dwek RA, Katinger H, Burton DR, Wilson IA (2003) Science 300:2065
Calarese DA, Lee H-K, Huang C-Y, Best MD, Astronomo RD, Stanfield RL, Katinger H, Burton DR, Wong C-H, Wilson IA (2005) Proc Natl Acad Sci USA 102:13372
Wang S-K, Liang P-H, Astronomo RD, Hsu T-L, Hsieh S-L, Burton DR, Wong C-H (2008) Proc Natl Acad Sci USA 105:3690
Joyce JG, Krauss IJ, Song HC, Opalka DW, Grimm KM, Nahas DD, Esser MT, Hrin R, Feng M, Dudkin VY, Chastain M, Shiver JW, Danishefsky S (2008) Proc Natl Acad Sci USA 105:15604
Grice P, Ley SV, Pietruszka J, Priepke HWM (1996) Angew Chem Int Ed 35:197
Grice P, Ley SV, Pietruszka J, Osborn HMI, Priepke HWM, Warriner SL (1997) Chem Eur J 3:431
Merritt JR, Naisang E, Fraser-Reid B (1994) J Org Chem 59:4443
Jiang L, Chan T-H, Nokami TK (2005) Can J Chem 83:693
Nokami T, Tsuyama H, Shibuya A, Nakatsutsumi T, Yoshida J (2008) Chem Lett 37:942
Adinolfi M, Iadonisi A, Ravidà A, Valerio S (2006) Tetrahedron Lett 47:2595
Jain RK, Liu X-G, Oruganti SR, Chandrasekaran EV, Matta KL (1995) Carbohydr Res 271:185
Takatani M, Ito Y (2006) Chem Asian J 1–2:64
Blattner R, Furneaux RH, Ludewig M (2006) Carbohydr Res 341:299
Lam SN, Gervay-Hague J (2005) J Org Chem 70:8772
Srivastava OP, Hindsgaul O (1987) J Org Chem 52:2869
Ratner DM, Plante OJ, Seeberger PH (2002) Eur J Org Chem:826
Du Y, Zhang M, Kong F (2001) Tetrahedron 57:1757
Jiang L, Chan T-H (2005) Can J Chem 83:693
Matsuo I, Wada M, Manabe S, Yamaguchi Y, Otake K, Kato K, Ito Y (2003) J Am Chem Soc 125:3402
Totani K, Ihara Y, Matsuo I, Koshino H, Ito Y (2005) Angew Chem Int Ed 44:7950
Xing Y, Ning J (2003) Tetrahedron Asymmetry 14:1275
Baeschlin DK, Chaperon AR, Charbonneau V, Green LG, Ley SV, Lücking U, Walther E (1998) Angew Chem Int Ed Engl 37:3423
Baeschlin DK, Chaperon AR, Green LG, Hahn MG, Ince SJ, Ley SV (2000) Chem Eur J 6:172
Ferguson MAJ, Homans SW, Dwek RA, Rademacher TW (1998) Science 239:753
Sharma DK, Smith TK, Weller CT, Crossman A, Brimacombe JS, Ferguson MA (1999) Glycobiology 9:415
Udenfriend S, Kodukula K (1995) Annu Rev Biochem 64:563
McConville MJ, Ferguson MAJ (1993) Biochem J 294:305
Ferguson MAJ (1997) Philos Trans R Soc London B 352:1295
Ali A, Vishwakarma RA (2010) Tetrahedron 66:4357
Shao N, Xue J, Guo Z (2004) Angew Chem Int Ed 43:1569
Yashunsky DV, Borodkin VS, Ferguson MAJ, Nikolaev AV (2006) Angew Chem Int Ed 45:468
Tailler D, Ferrieres V, Pekari K, Schmidt RR (1999) Tetrahedron Lett 40:679
Mayer TG, Schmidt RR (1999) Eur J Org Chem:1153
Mayer TG, Kratzer B, Schmidt RR (1994) Angew Chem Int Ed Engl 33:2177
Campbell AS, Fraser-Reid B (1995) J Am Chem Soc 117:10387
Madsen R, Udodong UE, Roberts C, Mootoo DR, Konradsson P, Fraser-Reid B (1995) J Am Chem Soc 117:1554
Roberts C, Madsen R, Fraser-Reid B (1995) J Am Chem Soc 117:1546
Murakata C, Ogawa T (1992) Carbohydr Res 235:95
Murakata C, Ogawa T (1992) Carbohydr Res 234:75
Murakata C, Ogawa T (1991) Tetrahedron Lett 32:671
Murakata C, Ogawa T (1990) Tetrahedron Lett 31:2439
Suzuki K, Matsumoto T (1993) J Syn Org Chem Jpn 51:718
Olafson RW, Thomas JR, Ferguson MAJ, Dwek RA, Chaudhuri M, Chang K-P, Rademacher TW (1990) J Biol Chem 265:12240
Düffels A, Green LG, Ley SV, Miller AD (2000) Chem Eur J 6:1416
Düffels A, Ley SV (1999) J Chem Soc Perkin Trans I:375
Cheung M-K, Douglas NL, Hinzen B, Ley SV, Pannecoucke X (1997) Synlett:257
Green L, Hinzen B, Ince SJ, Langer P, Ley SV, Warriner SL (1998) Synlett:440
Langer P, Ince SJ, Ley SV (1998) J Chem Soc Perkin Trans I:3913
Fankhauser C, Homans SW, Thomasoates JE, McConville MJ, Desponds C, Conzelmann A, Ferguson MAJ (1993) J Biol Chem 268:26365
Baeschlin DK, Green LG, Hahn MG, Hinzen B, Ince SJ, Ley SV (2000) Tetrahedron Asymmetry 11:173
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Gómez, A.M. (2010). A Survey of Ley’s Reactivity Tuning in Oligosaccharide Synthesis. In: Fraser-Reid, B., Cristóbal López, J. (eds) Reactivity Tuning in Oligosaccharide Assembly. Topics in Current Chemistry, vol 301. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_2010_112
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DOI: https://doi.org/10.1007/128_2010_112
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