121512-91-2

Basic information

• Product Name: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER
• Synonyms: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER
• CAS NO: 121512-91-2
• Molecular Formula: C₂₂H₃₃NO₁₂S
• Molecular Weight: 535.564
• Mol File: 121512-91-2.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER(121512-91-2)
• EPA Substance Registry System: PER-O-ACETYL-ALPHA-THIOETHYL-N-ACETYLNEURAMINIC METHYL ESTER(121512-91-2)

Safety Data

• Hazardous Substances Data: 121512-91-2(Hazardous Substances Data)

Upstream product

• 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 
• 811-51-8 sodium thioethylate 
• 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 
• 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 
• 75-08-1 ethanethiol 
• 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

• 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 articles and documents

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.

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.

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-