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, Kenichi Takao, Susumu Kobayashi

Research output: Contribution to journalArticle

58 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

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Disaccharides
Bleomycin
Mannose
Sugars
Anti-Bacterial Agents
Glycosylation
Acetals
Antineoplastic Agents
Derivatives
gulose

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose : Sugar moiety of antitumor antibiotic bleomycin. / Oshitari, Tetsuta; Shibasaki, Masakatsu; Yoshizawa, Takeshi; Tomita, Masahiro; Takao, Kenichi; Kobayashi, Susumu.

In: Tetrahedron, Vol. 53, No. 32, 11.08.1997, p. 10993-11006.

Research output: Contribution to journalArticle

Oshitari, Tetsuta ; Shibasaki, Masakatsu ; Yoshizawa, Takeshi ; Tomita, Masahiro ; Takao, Kenichi ; Kobayashi, Susumu. / Synthesis of 2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulopyranose : Sugar moiety of antitumor antibiotic bleomycin. In: Tetrahedron. 1997 ; Vol. 53, No. 32. pp. 10993-11006.
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