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

verfasst von

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.

Externe Organisation(en)

Technische Universität Clausthal

Typ

Artikel

Journal

Synlett

Band

1995

Seiten

767-769

Anzahl der Seiten

3

ISSN

0936-5214

Publikationsdatum

07.1995

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Organische Chemie

Elektronische Version(en)

https://doi.org/10.1055/s-1995-5051 (Zugang: Unbekannt)