874904-90-2

Basic information

• Product Name: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate
• Synonyms: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate
• CAS NO: 874904-90-2
• Molecular Weight: 662.571
• Mol File: 874904-90-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate(874904-90-2)
• EPA Substance Registry System: methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 2-(N-phenyl)trifluoroacetimidate(874904-90-2)

Safety Data

• Hazardous Substances Data: 874904-90-2(Hazardous Substances Data)

Upstream product

• 61881-19-4 2,2,2-trifluoro-N-phenyl-acetimidoyl chloride 
• 20298-34-4 methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl)onate 

Downstream Products

• 1028795-35-8 ethyl 2-O-benzoyl-6-O-benzyl-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-α-D-galacto-non-2-ulopyranonosyl]-1-thio-β-D-galactopyranoside 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 1028796-06-6 4-methoxyphenyl 6-O-benzyl-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-β-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 
• 1028795-49-4 4-methoxyphenyl 6-O-benzyl-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-α-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 
• 1028795-57-4 2-(trimethylsilyl)ethyl 6-O-(tert-butyldiphenylsilyl)-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-α-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 
• 1028796-13-5 2-(trimethylsilyl)ethyl 6-O-(tert-butyldiphenylsilyl)-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-β-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 
• 1028795-60-9 C₄₂H₅₅NO₁₆Si 
• 1028796-16-8 C₄₂H₅₅NO₁₆Si 
• 1028796-03-3 ethyl 6-O-benzyl-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-β-D-galacto-non-2-ulopyranonosyl]-1-thio-β-D-galactopyranoside 
• 1028795-46-1 ethyl 6-O-benzyl-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-α-D-galacto-non-2-ulopyranonosyl]-1-thio-β-D-galactopyranoside 
• 1028795-54-1 4-methoxyphenyl 6-O-(tert-butyldiphenylsilyl)-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-α-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 
• 1028796-10-2 4-methoxyphenyl 6-O-(tert-butyldiphenylsilyl)-3-O-[4,7,8,9-tetra-O-acetyl-5-(acetylamino)-3,5-dideoxy-1-methyl-D-glycero-β-D-galacto-non-2-ulopyranonosyl]-β-D-galactopyranoside 

Relevant articles and documents

Highly efficient α-sialylation by virtue of fixed dipole effects of N-phthalyl group: Application to continuous flow synthesis of α(2-3)-and α(2-6)-Neu5Ac-Gal motifs by microreactor

Highly α-selective sialylation of sialic acid N- phenyltrifluoroacetimidate with various galactose and lactose acceptors has been achieved by introducing the C-5 N-phthalyl group on the donor. The "fixed dipole effect" of the N-phthalyl group was proposed to explain the high reactivity and α-selectivity. The microfluidic system was applied to the present α-sialylation, which is amenable to large-scale synthesis. The N-phthalyl group was removed by treatment with methylhydrazine acetate, for which protocol can be readily applied to the synthesis of a variety of sialic acid-containing oligosaccharides. (Chemical Equation Presented). Copyright Taylor & Francis Group, LLC.