Catalytic Stereoselective Synthesis of 2-Amino-2-Deoxy-α-D-Glucopyranosides and Galactopyranosides
- 1 December 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 22 (12) , 2145-2148
- https://doi.org/10.1246/cl.1993.2145
Abstract
In the presence of a catalyst generated from SnCl4 and a silver salt, various 2-amino-2-deoxy-α-D-glucopyranosides or galactopyranosides are stereoselectively synthesized in good yields with high stereoselectivities through anomerization step starting from 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose or galactopyranose and alkyl trimethylsilyl ethers, respectively.Keywords
This publication has 10 references indexed in Scilit:
- Stereoselective total synthesis of glycopeptides bearing the dimeric and trimeric sialosyl-Tn epitopeCarbohydrate Research, 1992
- Solid phase synthesis of the fibronectin glycopeptide V(Gal?3GalNAc?)THPGY, its ? analogue, and the corresponding unglycosylated peptideGlycoconjugate Journal, 1991
- A novel glycoside anomerization catalyzed by trimethylsilyl bromide and zinc bromide in combination.CHEMICAL & PHARMACEUTICAL BULLETIN, 1991
- A highly stereoselective synthesis of di- and trimeric sialosyltn epitope: A partial structure of glycophorin ATetrahedron Letters, 1990
- Novel stereoselective glycosidation by the combined use of trityl halide and Lewis acid.CHEMICAL & PHARMACEUTICAL BULLETIN, 1990
- Synthesis of mono- and disaccharide amino-acid derivatives for use in solid phase peptide synthesisGlycoconjugate Journal, 1989
- Antigenes de groupe sanguinTetrahedron, 1985
- Blood group antigens: synthesis of TN glycopeptide related to human glycophorin AMInternational Journal of Peptide and Protein Research, 1983
- Advances in Selective Chemical Syntheses of Complex OligosaccharidesAngewandte Chemie International Edition in English, 1982
- The synthesis of derivatives of 3-O-(2-acetamido-2-deoxy-α-d-galacto-pyranosyl)-L-serine and-L-threonineCarbohydrate Research, 1980