Chiral Deuteration at C-5 of 1,5-Anhydropentofuranose Derivatives

Hiroshi OhruiDepartment of Food Chemistry, Faculty of Agriculture, Tohoku University, Amamiyamachi- Tsutsumidori 1–1, Sendai 980, Japan

Tsutami MisawaDepartment of Food Chemistry, Faculty of Agriculture, Tohoku University, Amamiyamachi- Tsutsumidori 1–1, Sendai 980, Japan

Hiroshi HoriDepartment of Food Chemistry, Faculty of Agriculture, Tohoku University, Amamiyamachi- Tsutsumidori 1–1, Sendai 980, Japan

Yoshihiro NishidaDepartment of Food Chemistry, Faculty of Agriculture, Tohoku University, Amamiyamachi- Tsutsumidori 1–1, Sendai 980, Japan

Hiroshi MeguroDepartment of Food Chemistry, Faculty of Agriculture, Tohoku University, Amamiyamachi- Tsutsumidori 1–1, Sendai 980, Japan

Abstract

Photobromination of 1,5-anhydropentofuranoses and subsequent metal deuteride reduction of the resulting 5-exo-bromides gave C-5 chirally deuterated 1,5-anhydropentofuranoses. The stereochemistry of the reduction is discussed in terms of the effects of substituents at C-2 and C-3 of 1,5-anhydropento-furanoses.

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Chiral Deuteration at C-5 of 1,5-Anhydropentofuranose Derivatives

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Chiral Deuteration at C-5 of 1,5-Anhydropentofuranose Derivatives

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