A CHEMOENZYMATIC SYNTHESIS OF D-ALLOSAMINE DERIVATIVES FROM TRI-O-ACETYL-D-GLUCAL

Authors
SUGAI T OKAZAKI H KUBOKI A OHTA H
Citation
T. Sugai et al., A CHEMOENZYMATIC SYNTHESIS OF D-ALLOSAMINE DERIVATIVES FROM TRI-O-ACETYL-D-GLUCAL, Bulletin of the Chemical Society of Japan, 70(10), 1997, pp. 2535-2540
Citations number
89
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
70
Issue
10
Year of publication
1997
Pages
2535 - 2540
Database
ISI
SICI code
0009-2673(1997)70:10<2535:ACSODD>2.0.ZU;2-U
Abstract
N-Acetyl-D-allosamine and its derivatives were synthesized from tri-O- acetyl-D-glucal based on lipase-catalyzed selective protection of prim ary alcohols, [3,3] sigmatropic rearrangement of allylic trichloroacet imidates, and stereoselective ruthenium-catalyzed dihydroxylation. In the course of this study, it was revealed that the Pseudomonas lipase- catalyzed acetylation occurred in a high yield (> 90%) exclusively at the primary alcohols of three Ferrier rearrangement products derived f rom tri-O-acetyl-D-glucal.