35510-36-2

Upstream product

• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 64-17-5 ethanol 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 20672-66-6 3,4,6-tri-O-benzyl-D-glucopyranose 
• 35526-01-3 ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 

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

Ionic liquids as phase transfer catalysts: Enhancing the biphasic extractive epoxidation reaction for the selective synthesis of β-O-glycosides

Ionic liquids promoted the direct epoxidation of glycals acting as PTC. 1,2-anhydrosugars were prepared by the oxidation of glycals under biphasic conditions with dimethydioxirane generated in situ from oxone/acetone and amphiphilic IL's as catalysts. β-O

Tandem epoxidation-alcoholysis or epoxidation-hydrolysis of glycals catalyzed by titanium(IV) isopropoxide or Venturello's phosphotungstate complex

Venturello's phosphotungstate complex and titanium(IV) isopropoxide [Ti(O-i-Pr)4] were successfully used as catalysts for the epoxidation-alcoholysis of glycals using hydrogen peroxide [H2O 2]. Reaction substrates included a range of variously protected glycals and different alcohols were used as solvents. Ti(O-i-Pr)4 was only effective in methanol as solvent, but gave methyl glycosides in high yields and high selectivities. The Venturello complex proved to be a very versatile and efficient catalyst. Apart from epoxidation-alcoholysis in alcoholic solvents it also showed activity in biphasic conditions to allow for glycosylation of long-chain alcohols and was very effective in the stereoselective dihydroxylation of benzylated glucal.

Expedient stereospecific synthesis of β-mannosides from a glucose- derived 1,2-orthoester

A new, stereospecific synthesis of β-mannosides from glucose-derived 1,2-orthoester has been developed using a simple four-step procedure. For the synthesis of β-D-Man-(1→6)-D-Gal, a 6-OH free galactose derivative was glycosylated with the orthoester to yield β-D-Glc-(1→6)-D-Gal; the Glc unit of which was epimerized into the β-mannoside in good yield.