SYNTHESIS OF 3-SUBSTITUTED (AZIDO, ACYLTHIO, CHLORO OR FLUORO)-2,3-DIDEOXY-D-ERYTHRO-PENTOSES AND 3-METHYL-3-SUBSTITUTED-2,3-DIDEOXY-D-ERYTHRO-PENTOSES

被引：0
|
作者：
RAIFELD, YE
NIKITENKO, AA
ARSHAVA, BM
MIKERIN, IE
ZILBERG, LL
VID, GY
LANG, SA
LEE, VJ
机构：
[1] JV ANGAREX,MOSCOW 117571,RUSSIA
[2] AMER CYANAMID CO,LEDERLE LABS,DIV MED RES,DEPT CHEM,INFECT DIS & MOLEC BIOL RES SECT,PEARL RIVER,NY 10965
来源：
TETRAHEDRON | 1994年 / 50卷 / 29期
关键词：
D O I：
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中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The enantioselective synthesis of 3-substituted and 3-methyl-3-substituted 2,3-dideoxy-D-erythro-pentoses from (3R,4R)-1,1-diethoxy-3,4-epoxypentane-5-ol, (3R,4R)-1,1-diethoxy-3,4-epoxy-3-methylpentane-5-ol and (2R,3R)-2,3-epoxy-5-hexen-1-ol is reported. The key step is cleavage of the oxirane ring by Ti(O-i-Pr)(3)X class reagents followed by selective cyclization of the acyclic acetals to the furanosides. Fluorination with the complex of titanium (IV) iso-propoxide - titanium (IV) fluoride provides an enantioselective synthesis of 3-fluoro-2,3-dideoxy-D-erythro-pentose and 3-fluoro-3-methyl-2,3-dedeoxy-D-erythro-pentose.
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页码：8603 / 8616
页数：14
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