121512-93-4

Basic information

• Product Name: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone
• Synonyms: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone
• CAS NO: 121512-93-4
• Molecular Weight: 615.612
• Mol File: 121512-93-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone(CAS DataBase Reference)
• NIST Chemistry Reference: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone(121512-93-4)
• EPA Substance Registry System: [methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosyl)onate] phenyl sulfone(121512-93-4)

Safety Data

• Hazardous Substances Data: 121512-93-4(Hazardous Substances Data)

Upstream product

• 108-98-5 thiophenol 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 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 
• 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 
• 118977-25-6 methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-galacto-2-nonulopyranoside)onate 

Downstream Products

• 511546-71-7 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-{1-[3S-(benzyloxycarbonyl)amino-4-(tetrahydro-2H-pyran-2-yloxy)-1-butanol]}-D-erythro-L-manno-nonanoate 
• 868527-85-9 4-acetoxy-5-acetylamino-2-({7-[acetyl-(4-chloro-benzoyl)-amino]-6-allyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl}-hydroxy-methyl)-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 525558-18-3 (2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-[1-hydroxy-3-(4-hydroxy-phenyl)-1-methyl-propyl]-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 525558-21-8 (2S,4S,5R,6R)-5-Acetylamino-2-(2-allyl-1-hydroxy-cyclohexyl)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 592544-41-7 4-acetoxy-5-acetylamino-2-{2-[3,4-diacetoxy-5-acetylamino-6-(2-benzyloxycarbonyl-2-benzyloxycarbonylamino-ethoxy)-tetrahydro-pyran-2-yl]-1-hydroxy-ethyl}-6-(1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 286939-02-4 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(R)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate 
• 286939-03-5 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2,6-anhydro-3,5-dideoxy-2-C-[(S)-hydroxy-[3-(p-methoxyphenyl 2,4,6-tri-O-benzyl-3-deoxy-β-D-galactopyranosidyl)]-methyl]-D-erythro-L-manno-nonate 

Relevant articles and documents

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.

Fast oxidation of thioglycosides to glycosyl sulfones using KMnO 4/CuSO4·5H2O under neutral reaction conditions

A rapid oxidation of thioglycosides to glycosyl sulfones has been achieved using a combination of KMnO4 and CuSO4·5H 2O in acetonitrile and water. This reaction protocol has many advantages compared to other methods availa