Synthesis of novel D-2′,3′-dideoxy-2′,3′-endo-methylene nucleosides

被引：28
|
作者：
Hong, JH [1 ]
Chun, BK [1 ]
Chu, CK [1 ]
机构：
[1] Univ Georgia, Coll Pharm, Dept Med Chem, Athens, GA 30602 USA
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 3-4期
关键词：
D O I：
10.1016/S0040-4039(97)10531-7
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Asymmetric synthesis of D2',3'-dideoxy-2',3'-endo-methylene nucleosides was achieved via the intermediate 2,3-endo-methylene pentofuranoyl chloride 6, which was prepared from 1,2:5,6-Di-O-isopropylidene-D-mannitol 1 with high stereoselectivity (only a chlorosugar). The SN2 type condensation of 6 with sodium salt of adenine and silyated N-4-benzoylcytosine gave the desired beta-nucleosides as major isomers (beta:alpha = 2.5:1 and 2:1, respectively). (C) 1997 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：225 / 228
页数：4
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