SYNTHESIS OF O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-L-GULOPYRANOSE - SUGAR MOIETY OF ANTITUMOR ANTIBIOTIC BLEOMYCIN

Authors
OSHITARI T SHIBASAKI M YOSHIZAWA T TOMITA M TAKAO K KOBAYASHI S
Citation
T. Oshitari et al., SYNTHESIS OF O-CARBAMOYL-ALPHA-D-MANNOPYRANOSYL)-L-GULOPYRANOSE - SUGAR MOIETY OF ANTITUMOR ANTIBIOTIC BLEOMYCIN, Tetrahedron, 53(32), 1997, pp. 10993-11006
Citations number
32
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
32
Year of publication
1997
Pages
10993 - 11006
Database
ISI
SICI code
0040-4020(1997)53:32<10993:SOO-S>2.0.ZU;2-D
Abstract
A new route to the disaccharide moiety )carbamoyl-alpha-D-mannopyranos yl)-L-gulopyranose) of the antitumor agent bleomycin was developed. Bo th the L-gulose synthon 21 and the 3-O-carbamoyl-D-mannose segment 30 were prepared from D-mannose in a regioselective manner by applying st annylene acetal methodology. Glycosylation of 21 with 30 proceeded smo othly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished. (C) 1997 Elsevier Science Ltd.