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

Tetsuta Oshitari, Masakatsu Shibasaki, Takeshi Yoshizawa, Masahiro Tomita, Ken Ichi Takao, Susumu Kobayashi

Research output: Contribution to journalArticle

60 Citations (Scopus)

Abstract

A new route to the disaccharide moiety (2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose) of the antitumor agent bleomycin was developed. 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.

Original languageEnglish
Pages (from-to)10993-11006
Number of pages14
JournalTetrahedron
Volume53
Issue number32
DOIs
Publication statusPublished - 1997 Aug 11
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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