3-氨基-3-脱氧-β-甘露吡喃糖苷的直接立体控制合成：氮保护基对立体选择性的重要性。
Direct stereocontrolled synthesis of 3-amino-3-deoxy-beta-mannopyranosides: importance of the nitrogen protecting group on stereoselectivity.
作者信息
Crich David, Xu Huadong
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. 2007 Jul 6;72(14):5183-92. doi: 10.1021/jo070473p. Epub 2007 Jun 13.
Abstract
The highly stereocontrolled synthesis of the 3-amino-3-deoxy-beta-mannopyranosides is achieved by means of thioglycoside donors protected with a 4,6-O-benzylidene or alkylidene acetal and a benzylidene imine group. Among the various nitrogen protecting groups investigated only the Schiff's base was found to give high beta-selectivity. N-Phthalimido and N-acetamido protected donors were found to be highly alpha-selective, whereas 3-azido-3-deoxy glycosyl donors gave intermediate selectivity. The reasons for the protecting group dependency are discussed in terms of the change in the O2-C2-C3-N3 torsional interaction on conversion of the covalent glycosyl triflates to the transient oxacarbenium ions.
摘要
通过用4,6-O-亚苄基或亚烷基缩醛和亚苄基亚胺基团保护的硫代糖苷供体实现了3-氨基-3-脱氧-β-甘露吡喃糖苷的高度立体控制合成。在所研究的各种氮保护基团中，仅发现席夫碱具有高β选择性。发现N-邻苯二甲酰亚胺和N-乙酰氨基保护的供体具有高α选择性，而3-叠氮基-3-脱氧糖基供体具有中等选择性。根据共价糖基三氟甲磺酸酯转化为瞬态氧鎓离子时O2-C2-C3-N3扭转相互作用的变化，讨论了保护基团依赖性的原因。
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