5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid

Base Information

• Chemical Name: 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid
• CAS No.: 114857-63-5
• Molecular Formula: C₁₈H₂₃NO₁₀
• Molecular Weight: 413.381
• Mol file: 114857-63-5.mol

Synonyms:5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid

Chemical Property of 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid

There total 4 articles about 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid 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: 72.0%

methyl 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate (270563-79-6) → 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid (114857-63-5) + N-acetyl neuraminic acid (19342-33-7)

Guidance literature:

With water; triethylamine; at 20 ℃; for 1.5h;

DOI:10.1016/S0968-0896(99)00325-9

Reference yield: 60.0%

N-acetyl neuraminic acid (6813-81-6,14120-72-0,19342-33-7,21646-00-4,82349-00-6,99395-98-9,99395-99-0,99396-00-6,102734-10-1,489-46-3,140671-47-2,140850-42-6,140850-43-7,140850-44-8,145375-13-9) + orthobenzoic acid trimethyl ester (707-07-3) → 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid (114857-63-5)

Guidance literature:

With toluene-4-sulfonic acid; In dimethyl sulfoxide; for 0.333333h; Ambient temperature;

DOI:10.1016/0008-6215(87)80269-0

Reference yield:

N-acetylneuraminic acid methyl ester (20298-35-5,22900-11-4,100678-43-1,109121-98-4,109122-00-1,119241-60-0,119241-61-1,119241-62-2) → 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic acid (114857-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / pyridine / 15 h / 20 °C

2: 72 percent / Et₃N; H₂O / 1.5 h / 20 °C

With pyridine; water; triethylamine; 1: Acylation / 2: Hydrolysis;

DOI:10.1016/S0968-0896(99)00325-9

upstream raw materials:

N-acetyl neuraminic acid

orthobenzoic acid trimethyl ester

methyl 5-acetamido-9-O-benzoyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosylonate

N-acetylneuraminic acid methyl ester

Downstream raw materials:

2-oxo-propionic acid