634197-71-0

Upstream product

• 852448-25-0 3,4,6-tri-O-benzyl-1,2-O-[1-(ethylsulfanyl)ethylidene]-α-D-glucopyranose 
• 106-45-6 para-thiocresol 
• 100-39-0 benzyl bromide 
• 51532-75-3 3,4,6-tri-O-benzyl-1,2-O-(1-methoxyethylidene)-α-D-glucopyranose 
• 3254-16-8 3,4,6-tri-O-acetyl-[1,2-O-(1-methoxyethylidene)]-α-D-glucopyranose 
• 83-87-4 D-glucose pentaacetate 
• 158852-31-4 3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 

Downstream Products

• 1360560-48-0 (3aS,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-[(benzyloxy)methyl]-2-ethyl-3aH,5H,6H,7H,7aH-pyrano[2,3-d][1,3]oxazole 
• 1427297-48-0 6-chlorohexyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 793672-65-8 4-methylphenyl 3,4,6-tri-O-benzyl-2-O-(2-iodo-1-(methyl 2,3,6-tri-O-benzyl-α-D-glucopyranos-4-O-yl)ethyl)-1-thio-β-D-glucopyranoside 
• 793672-55-6 p-methylphenyl 3,4,6-tri-O-benzyl-1-deoxy-1-thio-β-D-glucopyranoside 

Relevant academic research and scientific papers

2-: O-Benzyloxycarbonyl protected glycosyl donors: A revival of carbonate-mediated anchimeric assistance for diastereoselective glycosylation

By reviving an old idea, we demonstrate that alkoxycarbonyl groups can be used in glycosylation reactions to achieve full stereocontrol through participation of a carbonate moiety at O-2. Various benzyloxycarbonyl-protected glycosyl donors were prepared and used for efficient 1,2-trans glycosylation of base-labile compounds and the synthesis of glycosyl esters.

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD

(Chemical Equation Presented) Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary