Carbohydrate Research p. 83 - 90 (1981)
Update date:2022-07-29
Topics:
Salam, Mohammed A.
Behrman, Edward J.
Reaction of exo-3,4,6-tri-O-acetyl-1,2-O-(tert-butyl orthoacetyl)-α-D-glucopyranose with phosphoric acid and phosphorus pentaoxide in oxolane gave 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate.Treatment of the reaction mixture with aqueous lithium hydroxide gave the expected β-D-glucopyranosyl phosphate.However, neutralization with ammonium hydroxide gave exclusively the phosphoric diester, namely, bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate.Formation of the diester was traced to the phosphorus pentaoxide in the initial reaction-mixture.A study of solvents showed that phosphorylation of the ortho ester proceeds rapidly in a variety of ethers and N,N-dimethylamides.
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