107600-99-7

Upstream product

• 64508-50-5 2-methoxybenzoic anhydride 
• 81342-44-1 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-(2-(trimethylsilyl)ethoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 579-75-9 2-Methoxybenzoic acid 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 19879-84-6 tetraacetyl thioglucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 

Relevant academic research and scientific papers

Reversing Reactivity: Stereoselective Desulfurative 1,2- trans- O-Glycosylation of Anomeric Thiosugars with Carboxylic Acids under Copper or Cobalt Catalysis

We have discovered a new mode of reactivity of 1-thiosugars in the presence of Cu(II) or Co(II) for a stereoselective O-glycosylation reaction. The process involves the use of a catalytic amount of Cu(acac)2 or Co(acac)2 and Ag2CO3 as an oxidant in α,α,α-trifluorotoluene. Moreover, this protocol turned out to have a broad scope, allowing the preparation of a wide range of complex substituted O-glycoside esters in good to excellent yields with an exclusive 1,2-trans-selectivity. The late-stage modification of pharmaceuticals by this method was also demonstrated. To obtain a closer insight into the reaction mechanism, cyclic voltammetry was performed.

Improved synthesis of 1-O-acyl-β-D-glucopyranose tetraacetates

An improved synthesis of 1-O-acyl glucosyl esters that avoids the use of expensive Ag reagents as well as the hydrolysis of unstable glucosyl bromides is reported. Notably, β-configuration products were obtained exclusively in good yields.

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.

2-(Trimethylsilyl)ethyl glycosides. Transformation into the corresponding 1-O-acyl sugars.

(Trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranoside and (trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,6-tri-O-acetyl-4-O-[2-acetamido-4,6-di-O-ace tyl-2- deoxy-3-O-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-beta-D- galactopyranos