Selective Transesterification of 2,2,2-Trifluoroethyl Phosphates: Synthesis of Mixed Unsymmetrical Phosphates
Open Access
- 25 November 2019
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 21 (23) , 9779-9783
Abstract
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.Keywords
Funding Information
- Institute of Rheological Functions of Food
This publication has 64 references indexed in Scilit:
- Control of Phosphoryl Migratory Transesterifications Allows Regioselecive Access to Sugar PhosphatesOrganic Letters, 2013
- Synthesis of new organophosphorus compounds using the atherton–todd reaction as a versatile toolHeteroatom Chemistry, 2012
- Efficient Amidation and Esterification of Phosphoric Acid Using Cl3CCN/ Ph3PBulletin of the Korean Chemical Society, 2011
- Catalysis by supported Lewis acids: An efficient method for transesterification of phosphotriestersApplied Catalysis A: General, 2009
- Fluorinated phosphorus compoundsJournal of Fluorine Chemistry, 2000
- A Survey of Recent Progress in Phosphorus-Based Flame Retardants and Some Mode of Action StudiesPhosphorus, Sulfur, and Silicon and the Related Elements, 1999
- A Convenient Method for the Phosphorylation of Phenols with Diethyl CyanophosphonateSynthetic Communications, 1997
- A REVIEW OF THIRD PHASE FORMATION IN EXTRACTION OF ACTINIDES BY NEUTRAL ORGANOPHOSPHORUS EXTRACTANTSSolvent Extraction and Ion Exchange, 1996
- A Mild Preparation of Protected Phosphate Esters From AlcoholsThe Journal of Organic Chemistry, 1995
- A general transesterification method for the synthesis of mixed trialkyl phosphatesJournal of the American Chemical Society, 1977