O3 保护基对 4,6-O-苄叉基保护供体制备 C-吡喃甘露糖苷的立体选择性的影响。
Influence of the O3 protecting group on stereoselectivity in the preparation of C-mannopyranosides with 4,6-O-benzylidene protected donors.
机构信息
Centre de Recherche de Gif, Institut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91198 Gif-sur-Yvette, France.
出版信息
J Org Chem. 2010 Dec 17;75(24):8383-91. doi: 10.1021/jo101453y. Epub 2010 Nov 11.
Abstract
α-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.
摘要
α-C-吡喃葡萄糖苷和α-D-吡喃甘露糖苷可以通过 4,6-O-苄叉保护的 3-O-位带有酯基的葡萄糖基和甘露糖基硫糖苷与 C-亲核试剂在二苯砜、2,4,6-三特丁基嘧啶和三氟甲磺酸酐的活化作用下发生偶联反应，以 65-85%的收率得到。
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2
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Angew Chem Int Ed Engl. 2010 Apr 12;49(17):3049-52. doi: 10.1002/anie.200907178.
3
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4
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5
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6
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