4.4 Article

The synthesis of unsymmetrical S1-(3′-O-thymidine-O-methanephosphonyl)-S2-p-nitrophenyl disulfides and their reactions with triphenylphosphine

Journal

TETRAHEDRON LETTERS
Volume 41, Issue 8, Pages 1219-1222

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4039(99)02247-9

Keywords

nucleic acid analogues; phosphonic acids; derivatives; disulfides; stereoselectivity

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The reaction of thymidine 3'-methanephosphonothioic acid with p-nitrophenylsulfenyl chloride provides S-1 -(3'-O-thymidine-O-methanephosphonyl)-S-2-p-nitrophenyl disulfide which, in the presence of an excess of sulfenyl chloride and triphenylphosphine gives, in a stereospecific manner, thymidine 3'-(S-p-nitrophenyl methanephosphonodithioate). (C) 2000 Elsevier Science Ltd. All rights reserved.

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