1590365-50-6

Basic information

• Product Name: methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
• Synonyms: methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate
• CAS NO: 1590365-50-6
• Molecular Weight: 557.552
• Mol File: 1590365-50-6.mol

Chemical Properties

• CAS DataBase Reference: methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate(1590365-50-6)
• EPA Substance Registry System: methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate(1590365-50-6)

Safety Data

• Hazardous Substances Data: 1590365-50-6(Hazardous Substances Data)

Upstream product

• 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 
• 167084-05-1 methyl S-4-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-thio-D-glycero-α-D-galacto-2-nonulopyranosidonate 
• 1235555-29-9 methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate 
• 1151942-33-4 C₂₆H₃₁NO₁₂S 
• 108-93-0 cyclohexanol 
• 1246533-58-3 C₂₆H₃₁NO₁₂S 
• 132883-18-2 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl chloride 
• 374573-40-7 (2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant articles and documents

Comparative studies on the O-sialylation with four different α/β-oriented (N-acetyl)-5-N,4-O-carbonyl-protected p-toluenethiosialosides as donors

Four types of 5-N,4-O-carbonyl-protected p-toluenethiosialosides were synthesized and their couplings with different acceptors were thoroughly investigated. The results indicate that the sialyl donor structure, the amount of glycosyl acceptor, and the detailed promotion conditions have great influence on the sialylation stereoselectivties and product yields. Under the (p-Tol)2SO/Tf2O activation conditions, the glycosylations with simple alcohols provided declined α-selectivities and higher yields with increasing the amounts of acceptors from 1.1 equiv to 2.0 equiv. However, the outcome of same sialylation was independent of the relative amounts of sugar alcohol acceptors. With NIS/TfOH as promoter, the α-selectivities of the sialylations were significantly improved compared with the cases activated by (p-Tol)2SO/Tf2O. In general, the difference in configuration of N-acetylated sialyl donors (D2 and D4) has little effect on the sialylation yield and stereoselectivity. In contrast, the N-deacetylated α/β sialyl donors (D1 and D3) show complex sialylation profiles with different acceptors.