A Highly Stereoselective Synthesis of β-Glucosides from Pentaacylglucopyranose and Alkyl Silyl Ether by the Use of a Catalytic Amount of Active Species Generated from Methyltrichlorosilane and Silver Perchlorate
- 1 November 1992
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 21 (11) , 2105-2108
- https://doi.org/10.1246/cl.1992.2105
Abstract
An efficient catalytic β-glycosylation reaction starting from pentaacylglucopyranose and alkyl silyl ether was performed using an active species generated from MeSiCl3 and AgClO4. 1-O-Acetyl-2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranose stereoselectively reacted with alkyl silyl ethers with the assistance of neighboring effect to give the corresponding β-glucosides in high yields.Keywords
This publication has 4 references indexed in Scilit:
- Synthesis of Glycopeptides, Partial Structures of Biological Recognition Components [New Synthetic Methods (67)]Angewandte Chemie International Edition in English, 1987
- New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]Angewandte Chemie International Edition in English, 1986
- Advances in Selective Chemical Syntheses of Complex OligosaccharidesAngewandte Chemie International Edition in English, 1982
- Results and Problems of O‐Glycoside SynthesisAngewandte Chemie International Edition in English, 1974