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(1′R,2′S,5′R)‐Menthyl‐(5R)‐acetoxy‐1,3‐oxathiolan‐(2R)‐carboxylate: Synthesis and isomeric purity determination by HPLC
Author(s) -
Siddiqui M. Arshad,
Jin Haolun,
Evans Colleen A.,
Dimarco Marika P.,
Tse H. L. Allan,
Mansour Tarek S.
Publication year - 1994
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530060217
Subject(s) - chemistry , diastereomer , high performance liquid chromatography , lactol , acylation , carboxylate , chiral column chromatography , stereochemistry , carboxylic acid , chromatography , organic chemistry , lactone , catalysis
Chemoselective reduction of one isomer of the 1‐menthylester of 1,3‐oxathiolan‐5‐one‐2‐carboxylic acid produces a mixture of four lactol diastereomers from which the title compound was isolated after acylation. The isomeric purity and absolute stereochemistry were determined by spectroscopic methods, chiral HPLC techniques, and conversion to (−)‐2′‐deoxy‐3′‐thiacytidine (Lamivudine, 3TC TM ). © 1994 Wiley‐Liss, Inc.