76520-90-6

Upstream product

• 3282-30-2 pivaloyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 

Downstream Products

• 1261222-51-8 methyl 2,3-di-O-pivaloyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 186414-21-1 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-2-benzoyl-7-(2,2-dimethyl-propionyloxy)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester 
• 186414-27-7 2,2-Dimethyl-propionic acid (2R,4aR,6S,7R,8S,8aR)-7-(2,2-dimethyl-propionyloxy)-2-((R)-hydroxy-phenyl-methyl)-6-methoxy-3-(toluene-4-sulfonyl)-octahydro-pyrano[2,3-e][1,3]oxazin-8-yl ester 
• 186414-19-7 2,2-Dimethyl-propionic acid (2S,3R,4S,5R,6R)-3-(2,2-dimethyl-propionyloxy)-5-hydroxy-2-methoxy-6-[(toluene-4-sulfonylamino)-methyl]-tetrahydro-pyran-4-yl ester 
• 366801-67-4 methyl 2,3-di-O-pivaloyl-6-O-p-toluenesulfonyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Diastereoselective reduction of chiral N-tosyl 2-benzoyl-1,3-oxazines derived from D-glucose

Stereochemistry of reduction of the diastereomerically pure N-tosyl 2-benzoyl-1,3-oxazines prepared from D-glucose was investigated with various reducing agents. It was found that the stereachemical outcome is consistent with the Cram's chelation model where the ring oxygen atom is involved in chelation, not the tosyl oxygen as in the 5-membered oxazolidines.

Benzylidene Acetal Protecting Group as Carboxylic Acid Surrogate: Synthesis of Functionalized Uronic Acids and Sugar Amino Acids

Direct oxidation of the 4,6-O-benzylidene acetal protecting group to C-6 carboxylic acid has been developed that provides an easy access to a wide range of biologically important and synthetically challenging uronic acid and sugar amino acid derivatives in good yields. The RuCl3-NaIO4-mediated oxidative cleavage method eliminates protection and deprotection steps and the reaction takes place under mild conditions. The dual role of the benzylidene acetal, as a protecting group and source of carboxylic acid, was exploited in the efficient synthesis of six-carbon sialic acid analogues and disaccharides bearing uronic acids, including glycosaminoglycan analogues.