由L-高丝氨酸内酯便捷合成L-α-乙烯基甘氨酸
A Convenient Synthesis of L-α-Vinylglycine from L-Homoserine Lactone.
作者信息
Berkowitz David B, Smith Marianne K
机构信息
Department of Chemistry, University of Nebraska-Lincoln, Lincoln, NE 68588-0304, Fax + 1(402)4729402.
出版信息
Synthesis (Stuttg). 1996 Jan;1996(1):39-41. doi: 10.1055/s-1996-4177.
Abstract
A procedure for the synthesis of L-α-vinylglycine from L-homoserine lactone is described. The route developed is convenient (only one chromatography step is required) and efficient (72% yield; ≥95% optical yield over 4 steps). Key features include the use of acid-labile protecting groups for the amino (Boc) and carboxyl (diphenylmethyl ester) groups, and the use of the phenylselenolate equivalent derived from sodium borohydride and diphenyl diselenide for L-homoserine lactone cleavage.
摘要
本文描述了一种从L-高丝氨酸内酯合成L-α-乙烯基甘氨酸的方法。所开发的路线简便（仅需一步色谱步骤）且高效（产率72%；4步反应的光学产率≥95%）。关键特征包括对氨基（Boc）和羧基（二苯甲酯）使用对酸不稳定的保护基团，以及使用由硼氢化钠和二苯二硒化物衍生的苯硒醇盐等价物来裂解L-高丝氨酸内酯。
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