5-羟基-5-膦酰基己呋喃糖（α-羟基膦酸酯）脱氧反应中的立体选择性

Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates).

作者信息

Hanaya Tadashi, Sugiyama Ken-ichi, Kawamoto Heizan, Yamamoto Hiroshi

机构信息

Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan.

出版信息

Carbohydr Res. 2003 Jul 29;338(16):1641-50. doi: 10.1016/s0008-6215(03)00235-0.

DOI:10.1016/s0008-6215(03)00235-0

PMID:12873420

Abstract

The addition of dimethyl phosphonate to six different hexofuranos-5-uloses in the presence of DBU, followed by esterification with methoxalyl chloride and then radical reduction, afforded 5-deoxy-5-dimethoxyphosphinyl-D- and L-hexofuranoses. The stereoselectivity of the deoxygenation and possible transition-state models are discussed.

摘要

在1,8-二氮杂双环[5.4.0]十一碳-7-烯（DBU）存在下，向六种不同的己呋喃糖-5-酮中加入膦酸二甲酯，接着用甲氧甲酰氯进行酯化，然后进行自由基还原，得到5-脱氧-5-二甲基氧膦基-D-和-L-己呋喃糖。讨论了脱氧反应的立体选择性和可能的过渡态模型。