Synthesis of thioglycoside-based UDP-sugar analogues

被引：29
|
作者：
Zhu, XM [1 ]
Stolz, F [1 ]
Schmidt, RR [1 ]
机构：
[1] Univ Konstanz, Fachbereich Chem, D-78457 Constance, Germany
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 21期
关键词：
D O I：
10.1021/jo049077m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Arbuzov reaction of O-acetyl-protected glycosylthiomethyl chlorides with triethyl phosphite and then phosphonate ethyl ester cleavage with trimethylsilyl bromide afforded glycosylthiomethyl phosphonates 13, 18, 22, and 26. These intermediates could be readily transformed into the O-deprotected phosphonates 7-10 and into title compounds 1-4. Similarly, sulfonomethyl phosphonate moieties containing UDP-sugar analogues 5 and 6 were obtained.
引用
收藏
页码：7367 / 7370
页数：4
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