methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate

Base Information

• Chemical Name: methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate
• CAS No.: 855996-96-2
• Molecular Formula: C₂₆H₃₃NO₁₃
• Molecular Weight: 567.547
• Mol file: 855996-96-2.mol

Synonyms:methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate

Chemical Property of methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate

There total 4 articles about methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C26H34N2O14 + phenol (108-95-2,27073-41-2) → methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate (855996-96-2) + Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (128678-36-4)

Guidance literature:

With methyl trifluoromethanesulfonate; In dichloromethane; at 0 - 25 ℃; for 6h; Overall yield = 65 %; Overall yield = 9.8 mg; diastereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0035-1561461

Reference yield:

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester (84380-10-9) + phenol (108-95-2,27073-41-2) → methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate (855996-96-2) + Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (128678-36-4) + C20H27NO12

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In acetonitrile; at 0 ℃; for 3h; Overall yield = 76 percent; stereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1039/d0nj03044a

Reference yield:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) → methyl [phenyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosyl)]onate (855996-96-2) + Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate (128678-36-4)

Guidance literature:

Multi-step reaction with 2 steps

1: nitromethane / Inert atmosphere; Molecular sieve

2: methyl trifluoromethanesulfonate / dichloromethane / 6 h / 0 - 25 °C / Inert atmosphere

With methyl trifluoromethanesulfonate; In nitromethane; dichloromethane;

DOI:10.1055/s-0035-1561461

upstream raw materials:

methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

phenol

4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester

Downstream raw materials:

phenyl (5-acetamido-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranosylonic acid)

(2R,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-phenoxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester