New methods for the synthesis of N-benzoylated uridine and thymidine derivatives; a convenient method for N-debenzoylation

Carbohydr Res. 2002 Feb 18;337(4):369-72. doi: 10.1016/s0008-6215(01)00325-1.

Abstract

An improved procedure for the synthesis of N-benzoyl-2',3'-O-isopropylidene uridine via one-step selective N-benzoylation of 2',3' -O-isopropylidene uridine has been developed. An efficient synthetic route to N-benzoyl thymidine via initial tribenzoylation, followed by selective hydrolysis of the benzoates is also described. De-N-benzoylation of N-benzoylated thymidine and uridine derivatives can be conveniently effected under neutral conditions, by heating with benzyl alcohol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzoates / chemistry
  • Thymidine / chemistry*
  • Uridine / analogs & derivatives
  • Uridine / chemical synthesis*
  • Uridine / chemistry*

Substances

  • Benzoates
  • N-benzoyl-2',3'-O-isopropylidene uridine
  • Thymidine
  • benzoyl chloride
  • Uridine