Anti versus syn opening of epoxides derived from 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine with Me3Al: Factors controlling the stereoselectivity

Authors :: Kubota, Yutaka
Kunikata, Mayumi
Haraguchi, Kazuhiro
Hayashi, Mari
Ohkawa, Masaomi
Tanaka, Hiromichi
Source :: Journal of Organic Chemistry. Feb 3, 2006, Vol. 71 Issue 3, p1099, 5 p.
Publication Year :: 2006
Abstract: Reaction of Me3Al with the 3',4'-epoxides derived from 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine is investigated in detailed. Results reveal that the stereoselectivity of epoxide ring opening varied significantly upon changing the amount of Me2Al, the solvent, the O-silyl protecting group, and the reaction temperature.

Subjects :: Glycerin -- Chemical properties
Glycerol -- Chemical properties
Adenine -- Chemical properties
Epoxy compounds -- Chemical properties
Biological sciences
Chemistry

Tools