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Updated: Jul 19, 2026

Rapid One-step Enzymatic Synthesis and All-aqueous Purification of Trehalose Analogues
Published on: February 17, 2017
Anthracycline glycosides of 2,6-dideoxy-2-fluoro-alpha-L-talopyranose
1Department of Chemistry, American University, 4400 Massachusetts Avenue, NW, Washington, DC 20016, USA. carbchm@american.edu <carbchm@american.edu>
Abstract:
The methyl beta-glycoside of the title sugar, obtained from 2-deoxy-2-fluoro-beta-D-glucopyranose tetraacetate by a sequence with detailed characterization of all intermediates, was converted by acetolysis-bromination into 3,4-di-O-acetyl-2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl bromide, coupling of which with (7S,9S)-4-demethoxydaunomycinone afforded the 3,4-diacetate of 4-demethoxy-9-O-(2,6-dideoxy-2-fluoro-alpha-L-talopyranosyl)daunomycinone (19). The antitumor-active 19 was converted by way of its 14-bromo derivative into the 14-hydroxy analogue, the antitumor-active 4-demethoxyadriamycinone glycoside 21.
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