1214746-46-9

Upstream product

• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 1214746-48-1 methyl 4-O-benzoyl-2,3-di-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 1549988-85-3 C₁₉H₄₀O₅Si₂ 
• 1549988-88-6 (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-6-methoxycyclohex-2-enone 
• 1549988-96-6 (4S,5S,6S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2-iodo-6-methoxycyclohex-2-enone 
• 1549989-04-9 (3S,4S,5S)-4,5-bis((tert-butyldimethylsilyl)oxy)-2'-hydroxy-3-methoxy-4,5-dihydro-[1,1'-biphenyl]-2(3H)-one 

Relevant academic research and scientific papers

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.

Total synthesis of ribisin A

The first total synthesis of natural product ribisin A has been achieved in 11 steps from commercially available methyl α-d-glucopyranoside with 21.6% overall yield. The highly oxygenated benzofuran skeleton of this natural product was constructed, taking advantages of the inherent chirality of d-glucose, through the key reactions of Ferrier carbocyclization, Johnson iodination, Suzuki cross-coupling, and Wacker oxidative cyclization.

Regioselective control in the oxidative cleavage of 4,6-o-benzylidene acetals of glycopyranosides by dimethyldioxirane

"Chemical Equation Presentation" The oxidative cleavage of 4,6-O-benzylidene acetals of glycopyranosides using dimethyldioxirane (DMDO) leads to the corresponding hydroxy-benzoates in excellent yields. With a proper choice of the neighboring protecting groups, this oxidative fragmentation provides the 6- or 4-hydroxyl derivatives in a highly regioselective manner.