高立体选择性合成α-D-甘露吡喃糖基磷酸糖。
Highly stereoselective synthesis of alpha-D-mannopyranosyl phosphosugars.
机构信息
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, 1 avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
出版信息
J Org Chem. 2009 Dec 18;74(24):9576-9. doi: 10.1021/jo902254w.
Abstract
Alpha-mannopyranosyl phosphosugars are obtained in 61-90% yields from 4,6-O-benzylidene-protected mannosyl thioglycosides 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.
摘要
α-甘露糖基磷酸糖酯可从 3-O 位带有酯基官能团的 4,6-O-亚苄基保护的甘露糖基硫糖苷经与磷酸糖盐的偶联反应以 1-苯磺酰基哌啶、2,4,6-三特丁基嘧啶和三氟甲磺酸酐活化后以 61-90%的收率获得。由于存在非致死性酯基，仅观察到α-异构体的形成。
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