A highly efficient chemical synthesis of Rp and Sp adenyl(3′-5′)adenyl-o,o-phosphorothioate

John F. Marlier, Stephen J. Benkovic

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Abstract

A method is described for the chemical synthesis of the title compounds (Ap(S)A) via addition of elemental sulfur to a phosphite triester intermediate. Separation of the diastereomers of phosphorus could be accomplished on silica gel after removal of the terminal 5′-hydroxyl protecting group or on DEAE cellulose after complete deblocking. The triester to terminal 5′-hydroxyl. The overall yield of the synthesis (one coupling and four deblocking steps) is 30%.

Original languageEnglish (US)
Pages (from-to)1121-1124
Number of pages4
JournalTetrahedron Letters
Volume21
Issue number12
DOIs
Publication statusPublished - 1980

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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