61474-61-1

Upstream product

• 70893-32-2 2-benzothiazolyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 78687-40-8 methyl 2,3,4-tri-O-benzyl-6-O-(trimethylsilyl)-α-D-glucopyranoside 
• 74666-83-4 1-deoxy-1-(S-ethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 89025-46-7 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl fluoride 
• 104992-64-5 methyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 166733-02-4 S-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-N,N,N',N'-tetramethyl-N''-phenylphosphorodiamidimidothioate 
• 138904-01-5 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl 2-pyridinecarboxylate 
• 79386-43-9 diphenyl 2,3,4,6-tetra-O-benzyl-α-D-glucosyl phosphate 
• 143520-19-8 C₃₈H₄₇N₂O₇P 

Downstream Products

• 56632-57-6 methyl O-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->6)-2,3,4-tri-O-benzyll-α-D-glucopyranoside 

Relevant academic research and scientific papers

Tris(4-bromophenyl)aminium hexachloroantimonate-mediated glycosylations of selenoglycosides and thioglycosides. Evidence for single electron transfer?

Radical cation-initiated glycosylation reactions of phenyl selenoglycosides are described. Glycosylations of phenyl selenoglycosides effected by the single-electron-transfer (SET) reagent, tris(4-bromophenyl)aminium hexachloroantimonate (BAHA), are examined with primary and secondary hydroxyl acceptors. The corresponding reaction of an ethyl thioglycoside with a primary hydroxyl acceptor is also examined. Reactions are performed in the presence of the SET quenching reagent, 1,2,4,5-tetramethoxybenzene, to assess whether BAHA-mediated glycosylation reactions involve SET. These experiments indicate that the reactions are completely quenched in dichloromethane but only partially in acetonitrile. The results provide support for the SET mechanism but an alternative mechanism involving electrophilic activation cannot be discounted. The oxidation potentials of various selenoglycosides are determined by cyclic voltammetry. Copyright (C) 1998 Elsevier Science Ltd.

Ytterbium(III) tris[bis(perfluorobutylsulfonyl)amide] as a Lewis acid for glycosidations

The reaction of 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl acetate with alcohols in the presence of 5 mol% ytterbium(III) tris[bis(perfluorobutylsulfonyl)amide] as an activator afforded the corresponding glucopyranosides in good yields. This ytterbium complex also activated the benzylated glucosyl donors having trichloroacetoimidate, fluoride, and methoxyacetate as the leaving groups.

Stereoselective O-Glycosylations by Pyrylium Salt Organocatalysis**

Despite many years of invention, the field of carbohydrate chemistry remains rather inaccessible to non-specialists, which limits the scientific impact and reach of the discoveries made in the field. Aiming to increase the availability of stereoselective

Revisiting Glycosylations Using Glycosyl Fluoride by BF3·Et2O: Activation of Disarmed Glycosyl Fluorides with High Catalytic Turnover

Catalytic glycosylations with glycosyl fluorides using BF3·Et2O are presented. Glycosylations with both armed and disarmed donors were efficiently catalyzed by 1 mol% of BF3·Et2O in a nitrogen-filled glovebox without the use of dehydrating agents. Our finding is in sharp contrast with conventional BF3·Et2O-mediated glycosylations, where excess Lewis acid and additives are required. Mechanistic studies indicated that the chemical species formed by the reaction of in situ generated HF and glass vessels are involved in the catalytic cycle.

A Mechanistic Probe into 1,2-cis Glycoside Formation Catalyzed by Phenanthroline and Further Expansion of Scope

Phenanthroline, a rigid and planar compound with two fused pyridine rings, has been used as a powerful ligand for metals and a binding agent for DNA/RNA. We discovered that phenanthroline could be used as a nucleophilic catalyst to efficiently access high

A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides

Our group has previously reported that 3,3-difluoroxindole (HOFox) is able to mediate glycosylations via intermediacy of OFox imidates. Thioglycoside precursors were first converted into the corresponding glycosyl bromides that were then converted into the OFox imidates in the presence of Ag2O followed by the activation with catalytic Lewis acid in a regenerative fashion. Reported herein is a direct conversion of thioglycosides via the regenerative approach that bypasses the intermediacy of bromides and eliminates the need for heavy-metal-based promoters. The direct regenerative activation of thioglycosides is achieved under neutral reaction conditions using only 1 equiv. NIS and catalytic HOFox without the acidic additives.

Palladium(ii)-assisted activation of thioglycosides

Described herein is the first example of glycosidation of thioglycosides in the presence of palladium(ii) bromide. While the activation with PdBr2alone was proven feasible, higher yields and cleaner reactions were achieved when these glycosylat

ZnI2-Directed Stereocontrolled α-Glucosylation

Here we report a glucosylation strategy mediated by ZnI2, a cheap and mild Lewis acid, for the highly stereoselective construction of 1,2-cis-O-glycosidic linkages using easily accessible and common 4,6-O-tethered glucosyl donors. The versatility and effe

Automated Quantification of Hydroxyl Reactivities: Prediction of Glycosylation Reactions

The stereoselectivity and yield in glycosylation reactions are paramount but unpredictable. We have developed a database of acceptor nucleophilic constants (Aka) to quantify the nucleophilicity of hydroxyl groups in glycosylation influenced by the steric, electronic and structural effects, providing a connection between experiments and computer algorithms. The subtle reactivity differences among the hydroxyl groups on various carbohydrate molecules can be defined by Aka, which is easily accessible by a simple and convenient automation system to assure high reproducibility and accuracy. A diverse range of glycosylation donors and acceptors with well-defined reactivity and promoters were organized and processed by the designed software program “GlycoComputer” for prediction of glycosylation reactions without involving sophisticated computational processing. The importance of Aka was further verified by random forest algorithm, and the applicability was tested by the synthesis of a Lewis A skeleton to show that the stereoselectivity and yield can be accurately estimated.

Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis

Herein, o-(methoxycarbonyl)phenyl thioglycosides [or (methyl)salicyl 1-thioglycosides] were evaluated as non-malodorous thioglycoside alternatives. The o-methoxycarbonyl group was expected to assist in the departure of leaving group. Salicyl-type thioglyc