allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside
• CAS No.: 70834-40-1
• Molecular Formula: C₂₅H₂₇NO₈
• Molecular Weight: 469.491
• Mol file: 70834-40-1.mol

Synonyms:allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property of allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

There total 5 articles about allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside 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: 69.0%

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside (54400-75-8,64650-83-5,88903-97-3,116347-86-5,140849-88-3,144300-01-6,54400-77-0) + benzoyl chloride (98-88-4) → allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside (70834-40-1)

Guidance literature:

In tetrahydrofuran; pyridine; at -60 ℃; for 1h;

DOI:10.1246/bcsj.60.2197

Reference yield:

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline (10378-06-0,20757-53-3,35954-65-5,123483-77-2,134308-33-1) → allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside (70834-40-1)

Guidance literature:

Multi-step reaction with 3 steps

1: p-toluenesulfonic acid / CHCl₃ / Heating

2: 0.01M sodium methoxide

3: 69 percent / pyridine; tetrahydrofuran / 1 h / -60 °C

With sodium methylate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; chloroform;

DOI:10.1246/bcsj.60.2197

Reference yield:

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate (3006-60-8,4539-83-7,6730-10-5,7772-79-4,7784-54-5,10385-50-9,26151-16-6,76375-60-5,76375-61-6,95341-98-3,95341-99-4,134451-91-5,134451-96-0,136982-81-5,145375-11-7,148347-15-3,14086-90-9) → allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside (70834-40-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) hydrogen bromide, 2.) pyridine / 1.) CHCl₃, room temp., 2.) CHCl₃, 0 deg C, 10 min, 3.) CHCl₃, room temp.

2: p-toluenesulfonic acid / CHCl₃ / Heating

3: 0.01M sodium methoxide

4: 69 percent / pyridine; tetrahydrofuran / 1 h / -60 °C

With pyridine; hydrogen bromide; sodium methylate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; chloroform;

DOI:10.1246/bcsj.60.2197

upstream raw materials:

allyl 2-acetamido-2-deoxy-β-D-glucopyranoside

benzoyl chloride

2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate

2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline

Downstream raw materials:

allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-(2-tetrahydropyranyl)-β-D-glucopyranoside

allyl 2-acetamido-4-O-(4-azidobutyryl)-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

propyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside

allyl 6-O-<3,4,6-tri-O-acetyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranosyl>-3-O-benzoyl-4-O-benzyl-2-<(R)-3-benzyloxytetradecanoylamino>-2-deoxy-β-D-glucopyranoside