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Synthesis of 5′-O-(2-Azido-2-deoxy-α-D-glycosyl)nucleosides and Their Antitumor Activities

✍ Scribed by Gui-Sheng Zhang; Jie Chen; Ji-Mei Min; Li-He Zhang

Publisher
John Wiley and Sons
Year
2003
Tongue
German
Weight
163 KB
Volume
86
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The 1,3,4,6‐tetra‐O‐acetyl‐2‐azido‐2‐deoxy‐β‐D‐mannopyranose (4) or the mixture of 1,3,6‐tri‐O‐acetyl‐2‐azido‐2‐deoxy‐4‐O‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐galactopyranosyl)‐β‐D‐mannopyranose (10) and the corresponding α‐D‐glucopyranose‐type glycosyl donor 9/10 reacted at room temperature with protected nucleosides 12–15 in CH~2~Cl~2~ solution in the presence of BF~3~⋅OEt~2~ as promoter to give 5′‐O‐(2‐azido‐2‐deoxy‐α‐D‐glycosyl)nucleosides in reasonable yields (Schemes 2 and 3). Only the 5′‐O‐(α‐D‐mannopyranosyl)nucleosides were obtained. Compounds 21, 28, 30, and 31 showed growth inhibition of HeLa cells and hepatoma Bel‐7402 cells at a concentration of 10 μM in vitro.

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