Synthesis and enantiomeric purity determination of chiral 3-benzylglycidol, a key synthon for HIV protease inhibitors.
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.
Shum
W P
WP
Research and Development Department, ARCO Chemical Company, Newtown Square, Pennsylvania 19073-2387.
Chen
J
J
Cannarsa
M J
MJ
D000433:1-Propanol / Q000138:chemical synthesis / Q000302:isolation & purification; D000440:Butanols / Q000138:chemical synthesis / Q000302:isolation & purification*; D002851:Chromatography, High Pressure Liquid; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000302:isolation & purification*; D017320:HIV Protease Inhibitors / Q000138:chemical synthesis / Q000302:isolation & purification*; D020005:Propanols; D013237:Stereoisomerism
D000440:Butanols; D004852:Epoxy Compounds; D017320:HIV Protease Inhibitors; D020005:Propanols; C092094:3-benzylglycidol; D000433:1-Propanol; C004312:glycidol