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Synthesis and enantiomeric purity determination of chiral 3-benzylglycidol, a key synthon for hiv protease inhibitors

✍ Scribed by Wilfred P. Shum; Jian Chen; Michael J. Cannarsa

Publisher: John Wiley and Sons
Year: 1994
Tongue: English
Weight: 352 KB
Volume: 6
Category: Article
ISSN: 0899-0042
DOI: 10.1002/chir.530060813

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✦ Synopsis

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)-3benzylglycidol 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.

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