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(S)-Camphorsulfonic acid catalyzed highly stereoselective synthesis of pseudoglycosides.

Bioorganic & medicinal chemistry letters (2009-04-29)
Bala Kishan Gorityala, Shuting Cai, Jimei Ma, Xue-Wei Liu
ABSTRACT

A mild and efficient synthesis of pseudoglycosides has been developed using metal free (S)-camphorsulfonic acid. (S)-CSA acts as an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-D-glucal to 2,3-unsaturated O-glycosides. A wide range of biologically active natural products, alcohols and thiols could be coupled with glucal to give the desired pseudoglycosides in good to excellent yields with exclusive alpha-stereoselectivity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
(1S)-(+)-10-Camphorsulfonic acid, 99%
Sigma-Aldrich
(1R)-(−)-10-Camphorsulfonic acid, 98%
Sigma-Aldrich
Camphor-10-sulfonic acid (β), 98%
Sigma-Aldrich
(+)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)
Sigma-Aldrich
(−)-Camphor-10-sulfonic acid, purum, ≥98.0% (T)