Abstract
Thymidine, deoxycytidine, deoxyadenosine, and deoxyguanosine have been prepared with deuterium substitution at position 1' and at positions 1', 2', and 2'' from deuteriated deoxyribose. The synthetic strategy involved reduction of the bis(tert-butyldimethylsilyl) derivative of 2-deoxyribonolactone with Dibal-D followed by deprotection (HCl/MeOH and tetrabutylammonium fluoride) to give 1-deuterio methyl glycoside which was converted to the 1-deuterio 3,5-ditoluoyl methyl glycoside. Preliminary exchange of 2-deoxiribonolactone with NaOMe/MeOD brought about 2,2'-dideuteriation; treatment as above gave the 1,2,2'-trideuterio 3,5-ditoluoyl methyl glycoside
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