121512-91-2

Upstream product

• 108740-39-2 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 75-08-1 ethanethiol 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 145387-36-6 (2S,4S,5R,6R)-5-Acetylamino-2-ethylsulfanyl-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108-24-7 acetic anhydride 
• 811-51-8 sodium thioethylate 
• 1207887-24-8 methyl 2-(acetylsulfanyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-2,3,5-trideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosonate 
• 75-03-6 ethyl iodide 
• 104556-69-6 2-Thiosialic acid methyl ester peracetate 
• 6770-41-8 methyl 2-chloro-4,7,8,9-tetra-O-acetyl-N-acetyl-β-D-neuraminate 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 121512-94-5 O-ethyl S-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] dithiocarbonate 

Downstream Products

• 96520-15-9 benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 96520-16-0 benzyl O--(2-3)-2,6-di-O-benzyl-β-D-galactopyranoside 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 196951-49-2 methyl [(3-trifluoroacetamidopropyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 196951-45-8 methyl [(3-trifluoroacetamidopropyl)-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-pyranoside]-2-nonulosonate 
• 860783-54-6 (2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-6-((1R,2R)-3-benzyloxy-1,2-dihydroxy-propyl)-2-ethylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 860783-55-7 (2S,4S,5R,6R)-4-Benzoyloxy-6-((1R,2R)-3-benzyloxy-1,2-dihydroxy-propyl)-2-ethylsulfanyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 860783-56-8 (2S,4S,5R,6R)-5-Acetylamino-4-benzoyloxy-6-[(1S,2R)-3-benzyloxy-1,2-bis-(2-chloro-acetoxy)-propyl]-2-ethylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Concise Synthesis of 1-Thioalkyl Glycoside Donors by Reaction of Per-O-acetylated Sugars with Sodium Alkanethiolates under Solvent-Free Conditions

A relatively green method for synthesizing 1-thioalkyl glycosides has been developed, where sodium alkanethiolates were used to react with per-O-acetylated sugars instead of odorous alkyl mercaptans in the presence of BF3·Et2O without the use of solvents under mild conditions. Furthermore, we found that 1,2-trans-β-thioglycosides can be converted into corresponding 1,2-cis-α-thioglycosides in the presence of trifluoromethanesulfonic acid in nonpolar solvents under mild conditions. This provides a simple and efficient new approach for synthesizing challenging 1,2-cis-α-thioglycosides.

Triflic acid-mediated synthesis of thioglycosides

An efficient synthesis of thioglycosides from per-acetates in the presence of triflic acid is described. The developed protocol features high reaction rates and product yields. Some reactive sugar series give high efficiency in the presence of sub-stoichiometric trifluoromethanesulfonic acid (TfOH) in contrast to other known protocols that require multiple equivalents of Lewis acids to reach high conversion rates.

Novel strategies for the synthesis of unsymmetrical glycosyl disulfides

Novel strategies for the efficient synthesis of unsymmetrical glycosyl disulfides are reported. Glycosyl disulfides are increasingly important as glycomimetics and molecular probes in glycobiology. Sialosyl disulfides are synthesised directly from the chlorosialoside Neu5Ac2Cl, proceeding via a thiol-disulfide exchange reaction between the sialosyl thiolate and symmetrical disulfides. This methodology was adapted and found to be successfully applicable to the synthesis of unsymmetrical glucosyl disulfides under mild conditions.

Identification of an acetyl disulfide derivative in the synthesis of thiosialosides

The first report of the formation of an acetyl disulfide sialoside during the synthesis of thioglycosides is described. This compound is a by-product in the synthesis of the 2-thioacetyl sialoside commonly used in thioglycoside preparation. Our investigations into the identification of this novel disulfide are described.

Enhanced sialylating activity of O-chloroacetylated 2-thioethyl sialosides

It has been shown that O-chloroacetyl protecting groups enhance significantly sialylating activity of 2-thioethyl sialosides in model reactions of α(2-8)-sialylation. Ethyl 4,7,8,9-tetra-O-chloroacetyl-3,5-dideoxy-2- thio-5-trifluoroacetamido-D-glycero-α-

Mild stereoselective syntheses of thioglycosides under PTC conditions and their use as active and latent glycosyl donors

Mild and stereoselective arylthio glycoside syntheses were accomplished by inversion of configuration of glycosyl halides under phase transfer catalyzed conditions. Under such conditions, aryl α-thiosialosides having electron donating and withdrawing subs

Stereoselective synthesis of 2-thioglycosides of N-acetylneuraminic acid

Treatment of methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosonate (1) severally with thiophenol, phenylmethanethiol, and ethanethiol in the presence of boron trifluoride etherate gave the corresponding 2-thio-β-glycosides 3-5.Treatment of methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate (2) severally with thiophenol in the presence of N,N-di-isopropylethylamine, O-ethyl S-potassium dithiocarbonate, and O-ethyl S-potassium thiocarbonate gave the corresponding 2-thio-α-glycosides, 7, 10, and 11, of which 10 was converted into the ethyl 2-thio-α-glycoside 9 on heating with N,N-dimethylformamide-sodium iodide.The phenyl 2-thioglycosides 3 and 7 were converted into the corresponding sulfones.