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Stereoselectivity in deoxygenation of 5-hydroxy-5-phosphinyl-hexofuranoses (alpha-hydroxyphosphonates)
Tadashi Hanaya1, Ken-ichi Sugiyama, Heizan Kawamoto
1Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
Carbohydrate Research
|July 23, 2003
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.