methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate

Base Information

• Chemical Name: methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate
• CAS No.: 1354483-42-3
• Molecular Formula: C₁₉H₂₅NO₉
• Molecular Weight: 411.409
• Mol file: 1354483-42-3.mol

Synonyms:methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate

Chemical Property of methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate

There total 2 articles about methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate 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: 42.0%

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) + benzaldehyde (100-52-7) → methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate (1354483-42-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; for 20h; Inert atmosphere;

DOI:10.1039/c1ob06348k

Reference yield:

N-acetyl neuraminic acid (19342-33-7) → methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate (1354483-42-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlyst H⁺ resin / 72 h / 20 °C / Inert atmosphere

2: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 h / 20 °C / Inert atmosphere

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1039/c1ob06348k

Reference yield: 55.0%

methy 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosonate (1354483-42-3) → 5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galactononulopyranosic acid (1354483-43-4)

Guidance literature:

With trimethyltin(IV) hydroxide; In dichloromethane; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c1ob06348k

upstream raw materials:

N-acetylneuraminic acid methyl ester

benzaldehyde

N-acetyl neuraminic acid

Downstream raw materials:

5-acetamido-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galactononulopyranosic acid

5-acetamido-4-O-acetyl-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosic acid

5-acetamido-4-O-tert-butyldimethylsilyl-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosic acid

5-acetamido-4-O-tert-butyldimethylsilyl-8-O-acetyl-3,5-dideoxy-7,9-O-benzylidene-D-glycero-D-galacto-nonulopyranosic acid