160412-84-0

Upstream product

• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 108-93-0 cyclohexanol 
• 350985-71-6 phenyl 3,4,6-tri-O-benzyl-2-O-(1-para-methoxyphenylethenyl)-1-thio-β-D-glucopyranoside 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 350985-70-5 phenyl 3,4,6-tri-O-benzyl-2-O-para-methoxybenzoyl-1-thio-β-D-glucopyranoside 
• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 906360-08-5 cyclohexyl 3,4,6-tri-O-benzyl-2-O-(2,2-dimethyltrimethylene phosphonoyl)-β-D-glucopyranoside 
• 67-56-1 methanol 
• 152871-96-0 phenyl 1-deoxy-2-O-acetyl-3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Downstream Products

• 152141-30-5 (2R,3S,4S,5S,6R)-2-Cyclohexyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 244282-24-4 cyclohexyl 3,4,6-tri-O-benzyl-β-D-mannopyranoside 

Relevant academic research and scientific papers

Arylboronic acid-mediated glycosylation of 1,2-dihydroxyglucoses

- We explored direct dehydrative coupling of tetrahydro-2H-pyran-2,3-diol or a 1,2-dihydroxy sugar with various alcohols using a range of arylboronic acids. Among the catalysts, 2-borono-4-trifluoromethylbenzoic acid efficiently promoted acetalization of tetrahydro-2H-pyran-2,3-diol. Ferroceniumboronic acid showed the best catalytic activity for glycosylation of the 1,2-dihydroxy sugar. The major products were 1,2-cJi-a-D-glucopyranosides.

Simple and mild stereoselective O-glycosidation using 1,2-anhydrosugars under neutral conditions

The ring opening of α-D-1,2-anhydrohexapyranoses with phenols proceeded smoothly in ethyl acetate (neutral conditions) in the absence of metal ion catalysts or additives to stereoselectively furnish 1,2-cis-α-aryl glycosides as the major product and 1,2-t

Dialkylphosphates as stereodirecting protecting groups in oligosaccharide synthesis

(Chemical Equation Presented) Double duty: A phosphoric ester at the C2 position in glycosyl donors directs the glycosylation to occur selectively at the anomeric carbon atom with complete 1,2-trans selectivity. Since the phosphoric ester can be removed to give the hydroxy function, this group serves as a stereodirecting protecting group in oligosaccharide synthesis.

N-Iodosuccinimide-mediated intramolecular aglycon delivery

Enol ethers may be accessed via Tebbe methylenation of either 2-O acetates or para-methoxybenzoates. N-Iodosuccinimide may then be employed to achieve both tethering and thioglycoside activation allowing the stereoselective synthesis of α-glucosides and β-mannosides, either in a one or two step procedure.

Silica gel-catalyzed β-O-glucosylation of alcohols with 1,2-anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose

1,2-Anhydro-3,4,6-tri-O-pivaloyl-α-D-glucopyranose (1a) was allowed to react with alcohols in the presence of solid acids such as silica gel and zeolite HY, to afford β-O-glucosides stereoselectively. Several natural glucosides were synthesized by the application of the present resection.