112317-67-6

Basic information

• Product Name: Methyl-4,6-di-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside
• Synonyms: Methyl-4,6-di-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside;Methyl 4,6-O-benzylidene-2,3-di-O-pivaloyl-a-D-glucopyranoside;Methyl 4,6-O-[(R)-phenylmethylene]-alpha-D-glucopyranoside 2,3-bis(2,2-dimethylpropanoate)
• CAS NO: 112317-67-6
• Molecular Formula: C₂₄H₃₄O₈
• Molecular Weight: 450.525
• Product Categories: Carbohydrates
• Mol File: 112317-67-6.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Methyl-4,6-di-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl-4,6-di-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside(112317-67-6)
• EPA Substance Registry System: Methyl-4,6-di-O-benzylidene-2,3-di-O-pivaloyl-α-D-glucopyranoside(112317-67-6)

Safety Data

• Hazardous Substances Data: 112317-67-6(Hazardous Substances Data)

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 

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 articles and documents

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.