115236-85-6

Upstream product

• 4132-28-9 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 15715-58-9 triethylamine carbonate 

Downstream Products

• 125177-49-3 methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate), triethylammonium salt 
• 125177-47-1 methyl 3,4,6-tri-O-benzoyl-α-D-mannopyranoside 2-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-phosphate), triethylammonium salt 
• 125155-41-1 methyl 2,4,6-tri-O-benzoyl-α-D-mannopyranoside 3-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-phosphate), triethylammonium salt 
• 125177-49-3 methyl 2,3,6-tri-O-benzoyl-α-D-mannopyranoside 4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-phosphate), triethylammonium salt 

Relevant academic research and scientific papers

Hydrogenphosphonate synthesis of sugar phosphomonoesters

A highly efficient procedure for the phosphorylation of sugar hydroxy derivatives has been developed. A four-step sequence comprising H-phosphonate formation, pivaloyl chloride-mediated coupling with fluoren-9-ylmethanol, oxidation, and cleavage of the fiuoren-9-ylmethyl ester led to the sugar monophosphate derivatives 4a-g in 83-93% yield. The Royal Society of Chemistry 2000.

Application of the hydrogenphosphonate approach in the synthesis of glycosyl phosphosugars linked through secondary hydroxyl groups

The hydrogenphosphonate approach has been used in syntheses of methyl α-D-mannopyranoside 2-, 3-, and 4-(α-D-mannopyranosyl phosphate), benzyl β-D-galactopyranoside 2-(α-D-mannopyranosyl phosphate), and methyl β-D-galactopyranoside 4-(α-D-mannopyranosyl phosphate).Condensation of 2,3,4,6-tetra-O-benzyl- or 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl hydrogenphosphonate with suitable, partially acylated monohydroxy derivatives in the presence of Me3CCOCl, followed by oxidation of the resulting hydrogenphosphonate diesters with iodine, gave the O-protected phosphate diesters in yields of 67-87percent.Deprotection then gave the glycosyl phosphosugars.