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Synthesis of enantiomeric diethyl (1R,2R)- and (1S,2R)-1,2,3-trihydroxypropylphosphonates

✍ Scribed by Andrzej E. Wróblewski; Katarzyna B. Balcerzak

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
540 KB
Volume
54
Category
Article
ISSN
0040-4020

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✦ Synopsis

Addition of diethyl phosphite to 2,3-O-cyclohexylidene-D-glyceraldehyde catalyzed by triethylamine or fluorides led to ca. 35:65 mixtures of diethyl (IR,2R)-and (1S,2R)-2,3-O-cyclohexylidene-l,2,3trihydroxypropylphosphonates (4a) and (4b). Application of lithium diethylphosphonate only slightly improved diastereoselectivity. Through chromatographic separation of 4a and 4b the protected trihydroxypropyiphosphonates became available for the first time as pure enantiomers. The 1S configuration in the major diastereoisomer 4b was assigned on the basis of conformational and configurational analysis of 1,2-O-isopropylidene derivatives obtained from the title compounds.

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