✦ LIBER ✦

Syntheses and configurational assignments of the diastereomers of the 4-nitrophenyl esters of thymidine 3′-(N-phenyl phosphoramidate) and thymidine 5′-(N-phenyl phosphoramidate)

✍ Scribed by John A. Gerlt; Shujaath Mehdi; Jeffrey A. Coderre; William O. Rogers

Book ID: 104225772
Publisher: Elsevier Science
Year: 1980
Tongue: French
Weight: 259 KB
Volume: 21
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)93156-3

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✦ Synopsis

Sumnary:

The separated diastereomers of 3'-(4-nitrophenyl N-phenyl phosphoramidate)-5'-monomethoxytrityl thymidine and 3'-monomethoxytrityl-5'-(4-nitrophenyl N-phenyl phosphoramidate) thymidine have been prepared and their absolute configurations at phosphorus have been determined Recent work in this laboratory (1) and that of W. J. Stec (2) has shown that the sodium salts of N-phenyl phosphoramidate diesters react with [180]-carbonyl compounds (carbon dioxide (1) or benzaldehyde (2)) to yield oxygen chiral phosphodiesters; this reaction proceeds with retention of configuration at phosphorus. Because this reaction appears to be general, the syn-

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