Addition of Silyl- and Stannyl Anions to Carbohydrate-Derived 2,3-Dihydro-4H-pyran-4-ones

Facile Access to Glycosyl Silanes and -Stannanes

authored by

Andreas Kirschning, Jan Harders

Abstract

Conjugate addition of silyl cuprates 1a,b and lithio trialkyl stannanes 1c,d to monosaccharide-derived 2,3-dihydro-4H-pyran-4-ones 2-5 and 10 constitutes a new entry to silyl- and stannyl glycosides 6-9 and 11-13 which either may be employed for the Sila-Baeyer-Villiger oxidation to give pyranoses or are potential precursors for C-glycosides. The keto functionality in 8a/13a can efficiently be reduced to the alcohol in 14a or methylated to form 15 without affecting the anomeric silyl- or stannyl group.

External Organisation(s)

Clausthal University of Technology

Type

Article

Journal

Synlett

Volume

1996

Pages

772-774

No. of pages

3

ISSN

0936-5214

Publication date

1996

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Organic Chemistry

Electronic version(s)

https://doi.org/10.1055/s-1996-5513 (Access: Unknown)