One-step conversion of C-glycopyranosylnitromethanes to the corresponding methanal oximes

Authors
Pham-Huu, DP Petrusova, M BeMiller, JN Petrus, L
Citation
Dp. Pham-huu et al., One-step conversion of C-glycopyranosylnitromethanes to the corresponding methanal oximes, SYNLETT, (12), 1998, pp. 1319-1320
Citations number
22
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
12
Year of publication
1998
Pages
1319 - 1320
Database
ISI
SICI code
0936-5214(199812):12<1319:OCOCTT>2.0.ZU;2-W
Abstract
A novel method for preparation of C-glycopyranosyl-methanal oximes is descr ibed. Treatment of per-O-acetylated C-glycopyranosylnitromethanes of the be ta-D-gluco, beta-D-manno, beta-D-galacto, beta-D-xylo, and beta-L-rhamno co nfigurations with tributyltin hydride and a catalytic amount of 1,1'-azobis (cyclohexanecarbonitrile) afforded the corresponding methanal oximes in iso lated yields of 84-97%.