Synthesis of the Carbohydrate Moiety of Bleomycin. 1,3,4,6-Tetra-O-substituted L-Gulose Derivatives

Kiyoaki Katano, Pei In Chang, Alan Millar, Vince Pozsgay, David K. Minster, Tadaaki Ohgi, Sidney M. Hecht

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29 Scopus citations

Abstract

To facilitate the synthesis of the carbohydrate moiety of bleomycin [2-O-(3-O-carbamoyl-α-D-manno-pyranosyl)-L-gulopyranose] and its subsequent attachment to the remainder of the bleomycin molecule in a regio- and stereoselective fashion, a number of suitably protected gulose derivatives were prepared and their chemistry was studied. Key intermediates included 1,6-anhydro-3,4-di-O-benzyl-β-L-gulopyranose (12), 1,6-di-O-acetyl-3,4-di-O-benzyl-β-L-gulopyranose (24), benzyl 3,4,6-tri-O-benzyl-β-L-gulopyranoside (27), and 3,4-di-O-benzyl-1,6-dideoxy-1,6-(1-hydrazinyl-2-ylidene)-β-D-glucodialdehydo-1,5-pyranose (28).

Original languageEnglish (US)
Pages (from-to)5807-5815
Number of pages9
JournalJournal of Organic Chemistry
Volume50
Issue number26
DOIs
StatePublished - Dec 1985

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ASJC Scopus subject areas

  • Organic Chemistry

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