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An asymmetric synthesis of (R) and (S)-1-alkoxy-2,3-propanediols including precursors to platelet activating factor

✍ Scribed by Roy A. Johnson; Carmen E. Burgos; Eldon G. Nidy

Publisher: Elsevier Science
Year: 1989
Tongue: English
Weight: 560 KB
Volume: 50
Category: Article
ISSN: 0009-3084
DOI: 10.1016/0009-3084(89)90035-2

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✦ Synopsis

The titanium-assisted nucleophilic opening of glycidol with primary aliphatic alcohols gives l-alkoxy-2,3-propanediols. The titanium alkoxide used in the reaction should be the alkoxide of the alcohol used for the reaction. When optically active (S)-giycidol is used in the reaction, (S)-l-alkoxy-2,3-propanediols are obtained without loss of optical activity. When the reaction is cartied out at 70--75°C without solvent, the l-alkoxy-2,3-propanediols axe obtained in yields of 45--59%. The regioisomeric 2alkoxy-l,3-propanediols are found to the extent of 4---6% in the reaction. The optical purity of giycidol can be measured from the high field (500 MHz) nuclear magnetic resonance spectrum of the Mosher ester.

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