Highly Stereoselective Synthesis of α-D-Mannopyranosyl Phosphosugars
Highly Stereoselective Synthesis of α-D-Mannopyranosyl Phosphosugars
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DOI：
10.1021/jo902254w
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发表时间：
2009-12-18
影响因子：
3.6
通讯作者：
Picard, Sebastien
中科院分区：
文献类型：
--
作者：
Crich, David;Picard, Sebastien
由4，6-O-亚苄基保护的甘露糖硫代糖苷在3-O-位通过与磷糖的铵盐偶联反应，在1-苯磺酰基哌啶、2，4，6-三叔丁基嘧啶和三氟甲磺酸的活化作用下，以61-90%的产率得到α-甘露糖基磷糖。由于解臂酯基的存在，只观察到了α-异构体的形成。
alpha-Mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thio-glycosides bearing ester functionality in the 3-O-position by coupling reactions with ammonium salts of phosphosugars on activation with 1-benzenesulfinyl piperidine, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride. Due to the presence of the disarming ester group, only the formation of the alpha-isomer was observed.