Influence of the O3 Protecting Group on Stereoselectivity in the Preparation of C-Mannopyranosides with 4,6-O-Benzylidene Protected Donors
Influence of the O3 Protecting Group on Stereoselectivity in the Preparation of C-Mannopyranosides with 4,6-O-Benzylidene Protected Donors
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DOI：
10.1021/jo101453y
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发表时间：
2010-12-17
影响因子：
3.6
通讯作者：
Sharma, Indrajeet
中科院分区：
文献类型：
--
作者：
Crich, David;Sharma, Indrajeet
α-C-吡喃葡萄糖苷和吡喃甘露糖苷以65-85%的产率从在3-O-位带有酯官能团的4，6-O-亚苄基保护的葡糖基和甘露糖基硫代糖苷通过与C-亲核试剂在用二苯基亚砜、2，4，6-三叔丁基嘧啶和三氟甲磺酸酐活化时的偶联反应获得。
alpha-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.