141607-22-9

Upstream product

• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 838-85-7 diphenyl hydrogen phosphate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Downstream Products

• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 

Relevant academic research and scientific papers

O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing O-Acyl-Protected Glycosyl Donors

O-Glycosides of pivaloyl-protected glucose can be synthesized under neutral conditions in moderate yields by employing the pivaloylated β-glucosyl fluoride 2d and the respective β-benzyl phosphate 2e as glycosyl donors and 1 M solutions of LiClO4 in CH2Cl

Process for the preparation of glycosyl azides

A process for stereospecific preparation of glycosyl azides by reacting a metal azide with a glycosyl phosphate triester having the phosphate group cis to the adjacent C-2 substituent is disclosed.

Synthesis of glycosyl phosphates and azides

Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide togive the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids. Anomerically enriched diphenyl hexopyranosyl phosphate triesters have been prepared from O-alkyl and -acrylated hexopyranoses, using diphenyl chlorophosphate and 4-N,N-dimethylaminopyridine. Glycosyl phosphate triesters of D-gluco-, D-galacto-, D-manno, 2-acetamido-2-deoxy-D-gluco-, L-fuco-, and L-rhamno-pyranosyl derivatives have been obtained by this procedure. At temperatures 0° and above, and under thermodynamic control, diphenyl glycosyl phosphates cis to the pyranosyl C-2 substituent are formed predominantly, whereas at low temperatures and under kinetic control, glycosyl phosphate triesters having 1,2-trans stereochemistry are obtained. The β-glycosyl phosphate triesters of D-glucose and D-galactose derivatives are unstable and undergo anomerization to the α-glycosyl phosphate triesters, in contrast to the stable β-phosphate derivatives of L-rhamnose and D-mannose. These phosphate triesters have been deprotected to glycosyl phosphate triethylammonium salts, suitable for the preparation of other key biological derivatives, such as nucleotide sugars. In addition, the diphenyl phosphate groups at the anomeric center have been displaced by azide to give the glycosyl azides, key intermediates in the synthesis of glycosyl amino acids.