A note on the esterification of α‐D‐glucopyranosyl phosphate with benzyl halides
- 1 January 1985
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 104 (3) , 65-68
- https://doi.org/10.1002/recl.19851040302
Abstract
Esterification of the bis(tetrabutylammonium) salt of α‐D‐glucopyranosyl phosphate (1) with benzyl chloride or bromide in acetonitrile gave α‐D‐glucopyranosyl benzyl phosphate (2) in 80‐90% yield. An excess of benzyl chloride catalysed further reaction to a mixture of six phosphoric acid diesters via phosphoric acid triesters and D‐glucopyranosyl chlorides as intermediates. 1‐Bromohexane gave α‐d‐glucopyranosyl hexyl phosphate by the same method.Keywords
This publication has 9 references indexed in Scilit:
- Biosynthesis of a d-glucosyl polyisoprenyl diphosphate in particulate preparations of Micrococcus lysodeikticusCarbohydrate Research, 1983
- Erste strukturanaloga des antibiotikums moenomycin ATetrahedron, 1983
- .alpha.- and .beta.-Glycopyranosyl phosphates and 1,2-phosphates. Assignments of conformations in solution by carbon-13 and proton NMRBiochemistry, 1979
- Synthesis of methyl (or propyl) 2-acetamido-2-deoxy-α-D-glucopyranoside 6-(α-D-glucopyranosyl phosphate) and derivatives for the study of the phosphoric ester linkage in the Micrococcus lysodeikticus cell-wallCarbohydrate Research, 1978
- The Preparation of Mixed Dialkyl PhosphatesSynthesis, 1974
- Synthesis of glucose 1-phosphate-U-14C and specifically labeled sucroses using sucrose phosphorylaseAnalytical Biochemistry, 1972
- Organophosphorus esters—ITetrahedron, 1971
- THE MECHANISM OF THE ANOMERIZATION OF THE TETRA-O-ACETYL-D-GLUCOPYRANOSYL CHLORIDESCanadian Journal of Chemistry, 1965
- The β-Form of the Cori Ester (d-Glucopyranose 1-Phosphate)Journal of the American Chemical Society, 1942