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Synthesis and enantiomeric purity determination of chiral 3‐benzylglycidol, a key synthon for hiv protease inhibitors
Author(s) -
Shum Wilfred P.,
Chen Jian,
Cannarsa Michael J.
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.530060813
Subject(s) - synthon , chemistry , enantiomer , key (lock) , protease , combinatorial chemistry , stereochemistry , human immunodeficiency virus (hiv) , enantiomeric excess , enantioselective synthesis , organic chemistry , enzyme , catalysis , virology , ecology , biology
The detailed synthesis of (2R,3R)‐3‐benzylglycidol by the Sharpless asymmetric epoxidation route is described. The enantiomeric purity determination of this compound is complicated by the presence of small quantities of the diastereometric (2R,3S)‐3‐benzylglycidol from the asymmetric epoxidation of the cis ‐allylic alcohol, and the unreacted allylic alcohols that are not removed in the product isolation steps. We have developed a direct chiral HPLC method that can resolve all these components for the precise determination of enantiomeric excesses of chiral 3‐benzylglycidols. © 1994 Wiley‐Liss, Inc.