Synthesis of spacer-linked tail to tail dimers derived from a conformationally rigid aminodeoxysugar by olefin metathesis

authored by

Andreas Kirschning, Guang Wu Chen

Abstract

The preparation of new tail to tail dimers of bridged aminodeoxysugars 2 and 11 is described. The first key step in the synthesis is the formation of the aminomethyl bridge in the carbohydrate-derived monomer 7 which is achieved by silver promoted ring closure of methyl 3-acetamido-6-bromo-2,3,6- trideoxy α-D-glucoside 6. Secondly, olefin metathesis of the corresponding 4-O-allyl glycoside 9 constitutes a powerful tool for dimerization, which allows synthesis of 1,4-butanediol-linked tail to tail neooligosaccharides 2 and 11.

External Organisation(s)

Clausthal University of Technology

Type

Article

Journal

Synthesis

Pages

1133-1137

No. of pages

5

ISSN

0039-7881

Publication date

31.12.2000

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Catalysis, Organic Chemistry

Electronic version(s)

https://doi.org/10.1055/s-2000-6328 (Access: Unknown)