121512-90-1

Basic information

• Product Name: methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• Synonyms: methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate
• CAS NO: 121512-90-1
• Molecular Weight: 535.57
• Mol File: 121512-90-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate(121512-90-1)
• EPA Substance Registry System: methyl (ethyl 5-acetoamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate(121512-90-1)

Safety Data

• Hazardous Substances Data: 121512-90-1(Hazardous Substances Data)

Upstream product

• 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 
• 75-08-1 ethanethiol 

Downstream Products

• 242474-01-7 (3-trifluoroacetamidopropyl)-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O--α-D-D-galactopyranoside 
• 242474-00-6 (3-trifluoroacetamidopropyl)-2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O--α-D-D-galactopyranoside 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 242474-08-4 (3-trifluoroacetamidopropyl)-2-acetamido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-6-O--α-D-galactopyranoside 
• 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 

Relevant articles and documents

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.

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.