关于C2 - O2和C3 - O3键在4,6 - O - 亚苄基导向的β - 甘露吡喃糖基化和α - 葡糖吡喃糖基化中的影响
On the influence of the C2-O2 and C3-O3 bonds in 4,6-O-benzylidene-directed beta-mannopyranosylation and alpha-glucopyranosylation.
作者信息
Crich David, Vinogradova Olga
机构信息
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA.
出版信息
J Org Chem. 2006 Oct 27;71(22):8473-80. doi: 10.1021/jo061417b.
Abstract
The synthesis of 4,6-O-benzylidene-protected 2-deoxyarabino-, 3-deoxyarabino-, and 3-deoxyribothioglycosides is described and their glycosylation reactions, with activation by either 1-benzenesulfinyl piperidine/trifluoromethansulfonic anhydride or diphenyl sulfoxide/trifluoromethanesulfonic anhydride, studied. In contrast to the corresponding 4,6-O-benzylidene-protected glucosyl and mannosyl donors, which are alpha- and beta-selective, respectively, poor diastereoselectivity is observed in all cases. The reasons for this poor selectivity are discussed in terms of the interaction between the C2-O2 and C3-O3 bonds in the glucosyl and mannosyl donors and of the influence of this interaction on the ease of formation of the intermediate glycosyl oxacarbenium ions.
摘要
描述了4,6-O-亚苄基保护的2-脱氧阿拉伯糖基、3-脱氧阿拉伯糖基和3-脱氧核糖硫苷的合成，并研究了它们在1-苯亚磺酰基哌啶/三氟甲磺酸酐或二苯亚砜/三氟甲磺酸酐活化下的糖基化反应。与相应的分别具有α-和β-选择性的4,6-O-亚苄基保护的葡萄糖基和甘露糖基供体不同，在所有情况下均观察到较差的非对映选择性。从葡萄糖基和甘露糖基供体中C2-O2和C3-O3键之间的相互作用以及这种相互作用对中间体糖基氧碳鎓离子形成难易程度的影响方面讨论了这种选择性差的原因。
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