新型D-2'-脱氧-2'-C-二氟亚甲基-4'-硫代胞苷作为潜在抗肿瘤药物的合成。

Synthesis of novel D-2'-deoxy-2'-C-difluoromethylene-4'-thiocytidine as a potential antitumor agent.

作者信息

Lim Moo Hong, Kim Hea Ok, Moon Hyung Ryong, Chun Moon Woo, Jeong Lak Shin

机构信息

College of Pharmacy and Division of Chemistry and Molecular Engineering, Seoul National University, Seoul 151-742, Korea.

出版信息

Org Lett. 2002 Feb 21;4(4):529-31. doi: 10.1021/ol017112v.

DOI:10.1021/ol017112v

PMID:11843583

Abstract

[reaction: see text] 2'-Deoxy-2'-C-difluoromethylene-4'-thiocytidine (4) as a potential antitumor agent was synthesized starting from L-xylose via 2-deoxy-2-C-difluoromethylene-4-thiosugar as a key intermediate. An elimination product, 8, was always formed as the major product during removal of the protecting groups under acidic or basic conditions. However, utilizing neutral reaction conditions to remove the protecting groups afforded the desired product 4 exclusively.

摘要

[反应：见正文] 以L-木糖为起始原料，经关键中间体2-脱氧-2-C-二氟亚甲基-4-硫代糖合成了潜在的抗肿瘤药物2'-脱氧-2'-C-二氟亚甲基-4'-硫代胞苷（4）。在酸性或碱性条件下去除保护基团时，总是会形成一种消除产物8作为主要产物。然而，利用中性反应条件去除保护基团则仅得到所需产物4。