Anti versus syn opening of epoxides derived from 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine with Me3Al: factors controlling the stereoselectivity.
Upon epoxidation with dimethyldioxirane, the 2',5'-bis-O-silyl derivatives of 9-(3-deoxy-beta-D-glycero-pent-3-enofuranosyl)adenine gave the respective "3',4'-up" epoxides exclusively. Reaction between these epoxides and Me3Al was investigated in detail. It was found that the stereoselectivity of epoxide ring opening (anti versus syn) varied significantly upon changing the amount of Me3Al, the solvent, the O-silyl protecting group, and the reaction temperature. A possible reaction mechanism is proposed.
Kubota
Yutaka
Y
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Haraguchi
Kazuhiro
K
Kunikata
Mayumi
M
Hayashi
Mari
M
Ohkawa
Masaomi
M
Tanaka
Hiromichi
H
D017607:Aluminum Compounds / Q000737:chemistry*; D004852:Epoxy Compounds / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013696:Temperature
D017607:Aluminum Compounds; D004852:Epoxy Compounds