137063-47-9

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1449760-79-5 n-propyl-2,3,4-tri-O-benzyl-1-thio-α-L-fucopyranoside 
• 151909-89-6 1-O-acetyl-2,3,4-tri-O-benzyl-L-fucopyranose 
• 63734-12-3 methyl 6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 959774-86-8 p-methylphenyl 1-thio-β-L-fucopyranoside 
• 73-34-7 6-deoxy-L-galactose 
• 153658-86-7 (2S,3R,4R,5S,6R)-2-methyl-6-(p-tolylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-fucopyranose 
• 166592-73-0 methyl 2,3,4-tri-O-benzyl-6-O-(tert-butyldimethylsilyl)-α-D-glucopyranoside 
• 167612-35-3 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 
• 211801-54-6 p-methylphenyl 2,3,4-tri-O-benzyl-1-thio-β-L-fucopyranoside 

Relevant academic research and scientific papers

Palladium-Catalyzed C-S Bond Formation as a Tool for Latent-Active Glycosylation

A high-yielding palladium-catalyzed C-S cross-coupling is presented for utilization in carbohydrate chemistry as a key transformation for attachment of a second chelating sulfur atom that allows the exploitation of a latent-active glycosylation strategy w

A novel O-fucosylation strategy preactivated by (p-Tol)2SO/Tf2O and its application for the synthesis of Lewis blood group antigen Lewisa

Based on a preactivation strategy using (p-Tol)2SO/Tf2O, a new O-fucosylation method with thioglycoside as donor under mild conditions was reported. High yields and excellent α-stereoselectivities of the fucosylation were obtained wi

Glycosyl ortho-Methoxybenzoates: Catalytically Activated Glycosyl Donors with an Easily Removable and Recyclable Leaving Group

We describe the β-ortho-methoxybenzoate as a shelf stable and practical C-1 nucleofuge for catalytic chemical glycosylation in which the benzoic acid by-product can be easily removed, reisolated, and potentially recycled after the glycosylation reaction. This new type of glycosyl donor can be efficiently activated by a range of promoters, including Bi(OTf)3, Fe(OTf)3, TMSOTf (TMS = trimethylsilyl), and triflic acid, with low (10 mol-%) catalyst loadings. The donor shows higher reactivity than analogous benzoate, p-methoxybenzoate and p-cyano-o-methoxybenzoate donors. In glycosylation reactions with o-methoxybenzoate donors, the yields of disaccharide products were good to excellent for various glycosyl acceptors, including a carbohydrate-based secondary alcohol. Furthermore, β-selective mannosylation was achieved with a Crich-type donor at 0 °C to ambient temperature, without donor preactivation. The donor was also used for the first step of a one-pot two-step glycosylation to obtain a trisaccharide; the second coupling involved activation of a thioglycoside with NIS/TMSOTf (NIS = N-iodosuccinimide). We believe that this offers a good alternative to current protocols.

Glycosylation Reactions Using Phenyl(trifluoroethyl)iodonium Salts

Provided are methods for the preparation of glycosylation products, including those represented by formula I: [in-line-formulae]Sugar-O—R′??I[/in-line-formulae]comprising the step of combining R′—OH, a glycosyl sulfide glycosyl donor (“thioglycoside donor

An Air- and water-stable iodonium salt promoter for facile thioglycoside activation

The air- and water-stable iodonium salt phenyl(trifluoroethyl)iodonium triflimide is shown to activate thioglycosides for glycosylation at room temperature. Both armed and disarmed thioglycosides rapidly undergo glycosylation in 68-97% yield. The reaction

Bismuth(V)-mediated thioglycoside activation

A straightforward method utilizing a bismuth(V) compound was developed for the activation of thiopropylglycosides for coupling to various acceptors; good to excellent yields were obtained without applying additional additives/co-promoters. The method does

Dimethylformamide: An unusual glycosylation modulator

A simple solution: When N,N-dimethylformamide was used to direct the stereochemical course of glycosylation reactions, 1,2-cis glycosylation products were formed with excellent selectivity. A straightforward highly α-stereoselective glycosylation involvin

A new glycosylation method using glycosyl donors substituted by enol ether as a leaving group

Glycosyl donors having a leaving group of enol ether were easily prepared by the addition of the anomeric hydroxyl group of pyranose derivatives to α,β-unsaturated alkynic acid esters or -ketone. These glycosyl donors were selectively glycosidated with se