Iodine(III)-Promoted azide transfer to 3-deoxyglycals

authored by

Andreas Kirschning, Silvie Domann, Gerald Dräger, Lars Rose

Abstract

Direct iodine(III) promoted azide-transfer to 3-deoxyglycals 1-4 is described, leading to azidoglycals 5a,b-7a,b and hex-2-enopyranosyl azides 8a,b as main products. For the synthesis of precursor 1,5-anhydro-2,3,6-trideoxy-L-threo-hex-1-enitol (L-rhodinal) 3 a new high yielding synthetic variant of the literature is presented. The configuration of the new stereogenic center in 7a,b is determined by comparison of coupling constants with azidoglycal 15 which is obtained by a new synthesis employing a variant of the Mitsunobu reaction.

External Organisation(s)

Clausthal University of Technology

Type

Article

Journal

Synlett

Volume

1995

Pages

767-769

No. of pages

3

ISSN

0936-5214

Publication date

07.1995

Publication status

Published

Peer reviewed

Yes

ASJC Scopus subject areas

Organic Chemistry

Electronic version(s)

https://doi.org/10.1055/s-1995-5051 (Access: Unknown)