Abstract
The use of amino acid derivatives as building blocks in peptide synthesis is increasingly being recognized as a potential route for the development of pharmaceutical agents. Side chain protection of polyfunctional amino acids such as Ser, Thr, Tyr is viewed as being particularly important. Although these derivatives are commercially listed, they are expensive and not widely available. We describe here a practical large-scale synthesis oft-butyl introduced D-serine, one of the building blocks of zoladex, a peptide drug.
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Alan, A., Ian, B., Richard, F. W. J., Joanna, M. K., A new method for the preparation of tertiary butyl ethers and esters.Tetrahedron Lett., 29, 2483 (1988).
Carbrele, C., Langer, M., and Beck-Sickinger, A. G., Amino acid side chain attachment approach and its application to the synthesis of tyrosine-containing cyclic peptides.J. Org. Chem., 64, 4353 (1999).
Nefkens, G. H. L., Zwaneburg, B., Boroxazolidones as simultaneous protection of the amino and carboxyl group in α-amino acids.Tetrahedron Lett., 39, 2995 (1983).
Roby, J., Voyer, N., Protection of a protecting group: Preparation of stable N-silylatedt-butyl carbamates.Tetrahedron Lett., 38, 191 (1997).
Wang, J., Okada, Y., Wang, Z., Wang, Y., Li, W., Synthesis of-tert-butyl esters of aspartic acid and glutamic acid via b,b-difluoroboxazolidones.Chem. Pharm. Bull., 44 (11),2189–2191 (1996).
Wang, J., Okada, Y., Li, W., Yokoi, T., Zhu, J., 2,2-Difluro-1,3,2-oxazaboralidin-5-ones: novel approach for selective side-chain protection of serine and threonine.J. Chem. Soc. Perkin Trans., 1, 621 (1997).
Xi, N., Macro, A.C., A protection scheme for the preparation of acid chloride of serine and threonine.Tetrahedron Lett., 36, 6595 (1995).
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Choi, BE., Jeong, JH. Protection process of thetert-butyl group as a non-polar moiety of D-serine: Unexpected rearrangement. Arch Pharm Res 23, 564–567 (2000). https://doi.org/10.1007/BF02975241
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DOI: https://doi.org/10.1007/BF02975241