25320-98-3

Upstream product

• 6605-39-6 cyclohexyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 108-93-0 cyclohexanol 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 6605-39-6 cyclohexyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 34272-03-2 propargyl β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 57-50-1 Sucrose 
• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 6899-46-3 2,3,4,6-tetra-O-benzoyl-1-O-cyclohexyl-β-D-glucopyranoside 
• 74352-37-7 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(pyridin-2-ylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 6899-46-3 cyclohexyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Bimodal Glycosyl Donors Protected by 2- O-(ortho-Tosylamido)benzyl Group

A glucosyl donor equipped with C2-o-TsNHbenzyl ether was shown to provide both α- and β-glycosides stereoselectivity, by changing the reaction conditions. Namely, β-glycosides were selectively obtained when the trichloroacetimidate was activated by Tf2NH. On the other hand, activation by TfOH in Et2O provided α-glycosides as major products. This "single donor" approach was employed to assemble naturally occurring trisaccharide α-d-Glc-(1→2)-α-d-Glc-(1→6)-d-Glc and its anomers.

Biphasic catalysis with disaccharide phosphorylases: Chemoenzymatic synthesis of α- D -glucosides using sucrose phosphorylase

Thanks to its broad acceptor specificity, sucrose phosphorylase (SP) has been exploited for the transfer of glucose to a wide variety of acceptor molecules. Unfortunately, the low affinity (Km > 1 M) of SP towards these acceptors typically urges the addition of cosolvents, which often either fail to dissolve sufficient substrate or progressively give rise to enzyme inhibition and denaturation. In this work, a buffer/ethyl acetate ratio of 5:3 was identified to be the optimal solvent system, allowing the use of SP in biphasic systems. Careful optimization of the reaction conditions enabled the synthesis of a range of α-d-glucosides, such as cinnamyl α-d-glucopyranoside, geranyl α-d-glucopyranoside, 2-O-α-d-glucopyranosyl pyrogallol, and series of alkyl gallyl 4-O-α-d-glucopyranosides. The usefulness of biphasic catalysis was further illustrated by comparing the glucosylation of pyrogallol in a cosolvent and biphasic reaction system. The acceptor yield for the former reached only 17.4%, whereas roughly 60% of the initial pyrogallol was converted when using biphasic catalysis.

Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions

A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.

Green glycosylation promoted by reusable biomass carbonaceous solid acid: An easy access to β-stereoselective terpene galactosides

An efficient green protocol has been developed for the atom economic glycosylation of unprotected, unactivated glycosyl donors and glycosylation of glycosyl trichloroacetimidates with the aid of reusable eco-friendly biomass carbonaceous solid acid as catalyst. The Royal Society of Chemistry.

Efficient glycosylation of unprotected sugars using sulfamic acid: A mild eco-friendly catalyst

Sulfamic acid, a mild and environmentally benign catalyst has been successfully used in the Fischer glycosylation of unprotected sugars for the preparation alkyl glycosides. A diverse range of aliphatic alcohols have been used to prepare a series of alkyl glycosides in good to excellent yield.

Ionic liquid promoted atom economic glycosylation under Lewis acid catalysis

Straightforward glycosylation of various alcohols with unprotected and non-activated monosaccharides were performed under scandium triflate catalysis. Rate and yield of glycosylation were highly improved when using 1-butyl-3-methylimidazolium trifluoromethanesulfonate as a green solvent. This ionic liquid was allowed to be recycled at least three times without loss of activity. The possibility of drastically reducing the amounts of catalyst (down to 1 mol%) and aglycone (down to 1 equiv) when performing the reaction in ionic liquid opens new perspectives in O-glycosylation, as a direct coupling between an aglycone and free sugars.

Glycosylation using unprotected alkynyl donors

(Chemical Equation Presented) Gold(III) activation of unprotected propargyl glycosyl donors has been shown to be effective for the synthesis of saccharides. Terminal propargyl glycosides of glucose, galactose, and mannose required heating at reflux in ace

Synthesis of detergent O-glucosides by reverse hydrolysis in alcohol- water biphasic systems using α- and β-glucosidases

The α- and β-glucosidases showed significant O-glycosylation activity with glucose as substrate and with different alcohols both as reaction partners and solvents in reverse hydrolytic processes. With native glucosidases upscaling resulted in low yields due to heterogeneity of reaction mixtures. Immobilization of the enzymes on a modified polyacrylamide-type bead support (Acrylex C-100) increased enzyme stability resulting in higher yields and permitted to perform glucosylations on a larger scale. From these experiments O-alkyl glucosides were isolated in moderate yields.

The Substrate Specificity of Amyloglucosidase (AMG). Part IV. Hydroxycyclohexyl Glucosides

Cyclohexyl- and (1R,2R)- and (1S,2S)-hydroxycyclohexyl α-D-glucosides have been synthesised under halide-catalysed glycosylation reaction conditions.Furthermore, phenyl and 2-hydroxyphenyl α-D-glucopyranosides have been synthesised using fusion reactions in 60-70percent yield.Finally, methyl 4-O-(β-L-galactopyranosyl)-β-D-glucopyranoside has been prepared in high yield using silver triflate-promoted glycosylation conditions.All compounds have been characterised by NMR spectroscopy and their preferred solution conformations inferred from the NMR data and hard-sphere exo-anomeric effect calculations (HSEA).All the above-mentioned compounds have been investigated as potential substrates for the enzyme amyloglucosidase (AMG).The results show that only the compounds which have a preferred ground-state conformation similar to that of maltose can act as substrates for the enzyme.