Synthesis of the Disaccharide Moiety of Bleomycin. 2-O-(3-O-Carbamoyl-α-D-mannopyranosyl)-L-gulopyranose Derivatives

Kiyoaki Katano, Alan Millar, Vince Pozsgay, John L. Primeau, Sidney M. Hecht

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

The synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-mannopyranosyl)-L-gulo-pyranose] is described. A key parameter in defining a successful strategy was the lability of the carbamoyl group. Several approaches were investigated; the most successful involved the coupling of 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (19) and 2,4,6-tri-O-acetyl-3-O-carbamoyl-α-D-mannopyranosyl chloride (17) via the agency of silver trifluoromethanesulfonate and tetramethylurea. Also reported is the synthesis of l,6-di-O-acetyl-3,4-di-O-benzyl-2-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-L-gulopyranose (16), a dissacharide useful for the synthetic elaboration of decarbamoyl bleomycin.

Original languageEnglish (US)
Pages (from-to)2927-2932
Number of pages6
JournalJournal of Organic Chemistry
Volume51
Issue number15
DOIs
StatePublished - Jan 1 1986
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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