Abstract
Phosphoglycerides have been prepared in high yield by a three-step procedure utilising phosphoramidite intermediates. 2-Chloro-3-methyl-1,3,2-oxazaphosphospholidine 5 reacts with diacylglycerols to give cyclic phosphoramidites in near-quantitative yield. These are oxidised to the corresponding phosphates in very high yield with N2O4. The phosphates hydrolyse in water at ambient temperature, via exclusive P–N cleavage, to yield the target phospholipids. Similarly prepared from 2-chloro-1,3-dimethyl-1,3,2-diazaphospholidine 1 were the phosphoramidate lipid analogues. Spectral data on the intermediates and products are included and discussed.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 1
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