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

Facile Access to Glycosyl Silanes and -Stannanes

verfasst von

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.

Externe Organisation(en)

Technische Universität Clausthal

Typ

Artikel

Journal

Synlett

Band

1996

Seiten

772-774

Anzahl der Seiten

3

ISSN

0936-5214

Publikationsdatum

1996

Publikationsstatus

Veröffentlicht

Peer-reviewed

Ja

ASJC Scopus Sachgebiete

Organische Chemie

Elektronische Version(en)

https://doi.org/10.1055/s-1996-5513 (Zugang: Unbekannt)