667463-36-7

Usage

Uses

Used in Pharmaceutical Research:
PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER is used as a reagent for the asymmetric synthesis of sialic acid thioester phosphites, which are essential in the development of new drugs and therapies targeting various diseases and conditions.
Used in Chemical Synthesis:
In the chemical synthesis industry, PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER is used as a key intermediate for the production of complex organic molecules, particularly those involving sialic acid derivatives. Its unique structure allows for the creation of novel compounds with potential applications in various fields, including medicine, agriculture, and materials science.

Upstream product

• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycerol-β-D-galactonon-2-ulopyranoside)onate 
• 155155-64-9 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-phenylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108-24-7 acetic anhydride 
• 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 
• 108-98-5 thiophenol 

Downstream Products

• 1055325-36-4 4-tolylthio 4,7,8,9-tetra-O-acetyl-5-acetamido-2,3,5-trideoxy-2-phenylthio-D-glycero-β-D-galacto-non-2-ulopyranosonate 
• 1055325-34-2 benzylthio 4,7,8,9-tetra-O-acetyl-5-acetamido-2,3,5-tri-deoxy-2-phenylthio-D-glycero-β-D-galacto-non-2-ulopyranosonate 
• 1055325-37-5 4-nitrophenylthio 4,7,8,9-tetra-O-acetyl-5-acetamido-2,3,5-trideoxy-2-phenylthio-D-glycero-β-D-galacto-non-2-ulopyranosonate 
• 1055325-33-1 phenylthio 4,7,8,9-tetra-O-acetyl-5-acetamido-2,3,5-tri-deoxy-2-phenylthio-D-glycero-β-D-galacto-non-2-ulopyranosonate 
• 1055325-35-3 4-methoxyphenylthio 4,7,8,9-tetra-O-acetyl-5-acetamido-2,3,5-tri-deoxy-2-phenylthio-D-glycero-β-D-galacto-non-2-ulopyranosonate 

Relevant academic research and scientific papers

Thioester-assisted α-sialylation reaction

α-Selective sialylation reactions were carried out using novel sialic acid building blocks that possess a thioester auxiliary. In contrast to other arylthio- and benzylthioester derivatives, sialyl phosphite 1a (with the phenylthioester moiety) was employed as the α-selective building block, and was reacted with various primary alcohols, including the C6-OH group of galactose and glucose, with moderate to excellent α-selectivities. For C3-OH of the galactose, 4,6-di-O-benzylgalactal afforded desired α-linkage with excellent selectivity.

Approaches to intramolecular sialylation 2. * Synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid containing an unprotected carboxy group

Various approaches to the synthesis of per-O-acetylated thioglycosides of N-acetylneuraminic acid (Neu5Ac) containing an unprotected carboxy group starting from the corresponding methyl esters were comparatively studied. One-step demethylation of methyl t