Issue 26, 2011

Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-d-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

Abstract

The formation of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose was observed in the gold(I)-catalyzed glycosidation of peracetyl glucopyranosyl ortho-hexynylbenzoate; experiments with substrates bearing deuterium labeled 2-O-acetyl or 4-O-acetyl groups indicated that the orthoacetate was derived from the 4-O-acetyl group, which provided a direct evidence for the remote participation of the 4-O-acyl group in glycosylation.

Graphical abstract: Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-d-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

Supplementary files

Article information

Article type
Communication
Submitted
24 Mar 2011
Accepted
09 May 2011
First published
31 May 2011

Chem. Commun., 2011,47, 7515-7517

Identification of 3,6-di-O-acetyl-1,2,4-O-orthoacetyl-α-D-glucopyranose as a direct evidence for the 4-O-acyl group participation in glycosylation

Y. Ma, G. Lian, Y. Li and B. Yu, Chem. Commun., 2011, 47, 7515 DOI: 10.1039/C1CC11680K

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