82252-30-0

Upstream product

• 163916-60-7 3,4,6-Tri-O-benzyl-2-deoxy-α-D-glucopyranosyl fluoride 
• 108-93-0 cyclohexanol 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 82252-29-7 (E)-(2R,3R,4R)-1,3,4-Tris-benzyloxy-6-cyclohexyloxy-hex-5-en-2-ol 
• 82252-29-7 (Z)-(2R,3R,4R)-6-cyclohexyloxy-1,3,4-tribenzyloxy-5-hexen-2-ol 
• 160549-10-0 2,3,5-tri-O-benzyl-D-arabinofuranose 
• 132674-49-8 1-O-Acetyl-3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranose 
• 160549-11-1 3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 

Relevant academic research and scientific papers

Novel dehydrative glycosidations of 1-hydroxy sugars using a heteropoly acid

Novel and convenient dehydrative glycosidations of 1-hydroxy glycosyl donors have been developed. Several O-benzylated 1-hydroxy sugars are effectively cross-coupled with a variety of alcohols to give the corresponding O-glycosides in high yields with goo

Direct dehydrative glycosylation catalyzed by diphenylammonium triflate

Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.

Secondary amine salt catalyzed controlled activation of 2-deoxy sugar lactols towards alpha-selective dehydrative glycosylation

A new organocatalytic glycosylation method exploiting the lactol functionality has been disclosed. The catalytic generation of glycosyl oxacarbenium ions from lactols under forcible conditions via weakly Br?nsted-acidic, readily available secondary amine salts affects the diastereoselective glycosylation of 2-deoxypyranoses and furanoses. This operationally simple iminium catalyzed activation of 2-deoxy hemi-acetals is a potential alternative to the existing cumbersome methods that need specialized handling. The mechanisms for this unique transformation and kinetic/thermodynamic effects have been discussed based on both experimental evidence and theoretical studies.

Dehydrative glycosidations of 2-deoxysugar derivatives catalyzed by an arylboronic ester

An N-methylpyridinium-4-boronic ester acts as a catalyst for dehydrative glycosidations of 2-deoxy sugar-derived hemiacetals. The catalytic protocol is tolerant of functionalized acceptors, including alcohols bearing isopropylidene ketal, tert-butyl carbamate or benzyl carbamate groups. The results demonstrate that organoboron-catalyzed substitution reactions of alcohols, which have previously been conducted on π-activated (benzylic, allylic or propargylic) substrates, can also be used to achieve C–O bond formation from carbohydrate-derived hemiacetals.

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

The thio-additions of glycals were efficiently promoted by a stoichiometric amount of trimethylsilyl bromide (TMSBr) to produce S-2-deoxyglycosides under solvent-free conditions in good to excellent yields. In addition, with triphenylphosphine oxide as an additive, the TMSBr-mediated direct glycosylations of glycals with a large range of alcohols were highly α-selective.

Glycosylations of Glycals using N-Iodosuccinimide (NIS) and Phosphorus Compounds for Syntheses of 2-Iodo- and 2-Deoxyglycosides

The glycosylations of glycals and alcohols using N-iodosuccinimide (NIS) and a catalytic amount of PPh3 effectively proceeded under mild conditions to provide the corresponding 2-deoxy-2-iodoglycosides in high yields. The reactivity of the iodo

Environmentally benign β-stereoselective glycosidations of glycosyl phosphites using a reusable heterogeneous solid acid, montmorillonite K-10

Environmentally benign and stereoselective β-glycosidations of glycopyranosyl phosphites and alcohols using a reusable heterogeneous solid acid, montmorillonite K-10, as an activator have been developed. By these glycosidations, β-gluco-, 2-deoxy-β-gluco-

Stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia, for the direct syntheses of α- and β-manno- and 2-deoxyglucopyranosides

Novel α- and β-stereocontrolled glycosidations using a heterogeneous solid acid, sulfated zirconia (SO4/ZrO2), as an activator have been developed. The glycosidations of manno- and 2-deoxyglucopyranosyl α-fluorides with several alcoh

A novel promoter, heteropoly acid, mediated chemo- and stereoselective sulfoxide glycosidation reactions

The chemo- and stereoselective glycosidations of sulfinylglycosides and alcohols using a heteropoly acid, H3PW12O40, as a new promoter have been developed. (C) 2000 Elsevier Science Ltd.

Novel stereocontrolled glycosidations of 2-deoxyglucopyranosyl fluoride using a heterogeneous solid acid, sulfated zirconia (SO4[ZrO2)

Novel stereocontrolled glycosidations of a 2-deoxy-α-D-glucopyranosyl fluoride using a heterogeneous and environmentally friendly solid acid, sulfated zirconia (SO4/ZrO2), have been developed. The glycosidations of the perbenzylated