Journal of Organic Chemistry p. 1100 - 1103 (1993)
Update date:2022-08-03
Topics:
Goering, Brad K.
Lee, Kwangjin
An, Byungjae
Cha, Jin K.
A stereoselective synthesis of perdeuterated deoxyribofuranoside (1) has been developed starting from known methyl 4-(2'-tetrahydropyranyloxy)-2-butynoate.The synthetic strategy involved the Sharpless asymmetric epoxidation of alcohol 7, followed by a tandem epoxide isomerization and opening with NaCN.The resulting lactone 4b was then reduced via its TBDMS derivative with Dibal-D and subsequently converted to perdeuterated deoxyribofuranoside (1).
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