667463-36-7

Basic information

• Product Name: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER
• Synonyms: β-Neuraminic acid, N-acetyl-2-S-phenyl-2-thio-, 4,7,8,9-tetraacetate;4,?7,?8,?9-?Tetraacetate-N-?acetyl-?2-?S-?phenyl-?2-?thio-β-?neuraminic Acid
• CAS NO: 667463-36-7
• Molecular Formula: C₂₅H₃₁NO₁₂S
• Molecular Weight: 583.6
• Mol File: 667463-36-7.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(667463-36-7)
• EPA Substance Registry System: PER-O-ACETYL-ALPHA-THIOPHENYL-N-ACETYLNEURAMINIC METHYL ESTER(667463-36-7)

Safety Data

• Hazardous Substances Data: 667463-36-7(Hazardous Substances Data)

Usage

Uses

4,?7,?8,?9-?Tetraacetate-N-?acetyl-?2-?S-?phenyl-?2-?thio-β-?neuraminic Acid is a useful reagent for asymmetric synthesis of sialic acid thioester phosphites.

Upstream product

• 108-98-5 thiophenol 
• 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 
• 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 
• 108-24-7 acetic anhydride 

Downstream Products

• 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 
• 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 
• 1055325-36-4 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 

Relevant articles and documents

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.