58526-05-9

Basic information

• Product Name: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate
• Synonyms: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate
• CAS NO: 58526-05-9
• Molecular Weight: 428.287
• Mol File: 58526-05-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate(58526-05-9)
• EPA Substance Registry System: 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl phosphate(58526-05-9)

Safety Data

• Hazardous Substances Data: 58526-05-9(Hazardous Substances Data)

Upstream product

• 77895-06-8 bis(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) phosphate 

Downstream Products

• 14034-70-9 β-D-glucopyranosyl 
• 59-56-3 β-D-glucose 1-phosphate 

Relevant articles and documents

SYNTHESIS OF GLYCOSYL PHOSPHATES FROM SUGAR ORTHO ESTERS: FORMATION OF BIS(2,3,4,6-TETRA-O-ACETYL-β-D-GLUCOPYRANOSYL) PHOSPHATE, AND THE EFFECT OF SOLVENTS ON THE SYNTHESIS OF β-D-GLUCOPYRANOSYL PHOSPHATE

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.