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Synthesis of antitumor-active 7-O-(2,6-dideoxy-2-fluoro-α-l-talopyranosyl)-daunomycinone and -adriamycinone

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
169
Identifiers
DOI: 10.1016/0008-6215(87)80243-4

Abstract

Abstract The title compounds ( 17 and 23) were prepared by coupling 3,4-di- O-acetyl-2,6-dideoxy-2-fluoro-α- l-talopyranosyl bromide ( 15) with daunomycinone. The key step in the preparation of 15 was the epoxide-ring opening of methyl 2,3-anhydro-4- O-benzyl-6-deoxy-α- l-gulopyranoside with KHF 2 in ethylene glycol, whereupon 2-fluoro-α- l-idopyranoside was obtained. Compounds 17 and 23 showed strong anti-tumor activity.

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