Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates

A selective transesterification starting with tris­(2,2,2-trifluoroethyl) phosphate has been developed. This method involves a three-step substitution for 2,2,2-trifluoroethoxy groups and enables the facile synthesis of mixed unsymmetric phosphate triesters from three different alcohols. The substit...

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Bibliographic Details
Published in:Organic letters 2019-12, Vol.21 (23), p.9779-9783
Main Authors: Tsubaki, Kouta, Shimooka, Hirokazu, Kitamura, Mitsuru, Okauchi, Tatsuo
Format: Article
Language:English
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Summary:A selective transesterification starting with tris­(2,2,2-trifluoroethyl) phosphate has been developed. This method involves a three-step substitution for 2,2,2-trifluoroethoxy groups and enables the facile synthesis of mixed unsymmetric phosphate triesters from three different alcohols. The substitution of the trifluoroethoxy group at the phosphorus proceeds selectively in the presence of DBU or lithium alkoxides. This method can be applied for the preparation of phospholipids.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.9b04003