650601-57-3Relevant articles and documents
Synthesis of dinucleotide thiophosphoramidates as anti-HIV new prodrugs
Lin, Changxue,Fu, Hua,Tu, Guangzhong,Zhao, Yufen
, p. 1989 - 1994 (2007/10/03)
Sequential transesterification of diphenyl phosphite with 5′-O-(4,4′-dimethoxytrityl)thymidine (1) and hydrogen sulfide gave O-[5′-O-(4,4′-dimethoxytrityl)thymidine-3′-yl] H-thiophosphonate (2), and subsequent condensation of 2 with AZT or d4T in the presence of diphenyl chlorophosphoate provided the dinucleotide H-thiophosphonates 3 or 3′. The Antherton-Todd reaction of 3 or 3′ with L-amino acid methyl ester in a solution of CCl4-Et 3N-H2O-MeCN gave the dinuleotide thiophosphoramidates 4 or 4′, and removal of the dimethoxytrityl protecting group in formic acid yielded the target products AZT/d4T thiophosphoramidates 5 and 5′.