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Synthesis of 2-O-(3-O-carbamoyl-α-d-mannopyranosyl)-l-gulopyranose: Sugar moiety of antitumor antibiotic bleomycin

✍ Scribed by Tetsuta Oshitari; Masakatsu Shibasaki; Takeshi Yoshizawa; Masahiro Tomita; Ken-ichi Takao; Susumu Kobayashi

Publisher: Elsevier Science
Year: 1997
Tongue: French
Weight: 892 KB
Volume: 53
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(97)00360-8

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✦ Synopsis

A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-a-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was develolfed. Both 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 stannylene acetal methodology. Glycosylation of 21 with 30 proceeded smoothly, and further conversion to disaccharide derivatives (33 and 34) was successfully accomplished.

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