Direct synthesis of methyl phosphoramidates in carbohydratesElectronic supplementary information (ESI) available: Experimental procedures, characterisation data of new compounds, and copies of NMR spectra. See DOI: 10.1039/c5ob01017a

A direct installation of a methyl phosphoramidate group by using methyl benzylphosphoramidochloridate into carbohydrates and amino acid is described. This one-step synthesis is efficient for both primary and secondary alcohols and exhibited excellent regioselectivity and functional group compatibili...

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Bibliographic Details
Main Authors Dhurandhare, Vijay M, Mishra, Girija Prasad, Lam, Sarah, Wang, Cheng-Chung
Format Journal Article
LanguageEnglish
Published 02.09.2015
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Summary:A direct installation of a methyl phosphoramidate group by using methyl benzylphosphoramidochloridate into carbohydrates and amino acid is described. This one-step synthesis is efficient for both primary and secondary alcohols and exhibited excellent regioselectivity and functional group compatibility. Formation of a single diastereomer is observed in certain cases. The N -benzyl protecting group on methyl phosphoramidates is easily removed under mild conditions. Direct one-step synthesis with high regioselectivity, 16 examples up to quantitative yield.
Bibliography:10.1039/c5ob01017a
Electronic supplementary information (ESI) available: Experimental procedures, characterisation data of new compounds, and copies of NMR spectra. See DOI
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob01017a