methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside

Base Information

• Chemical Name: methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside
• CAS No.: 176691-04-6
• Molecular Formula: C₃₇H₄₄N₂O₁₅S
• Molecular Weight: 788.827
• Mol file: 176691-04-6.mol

Synonyms:methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside

Chemical Property of methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside

There total 6 articles about methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-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: 63.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose (51450-09-0) + methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside (176691-03-5) → methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside (176691-04-6)

Guidance literature:

With 1,4-dithio-erythritol; Cysteamine; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1039/P19960000581

Reference yield:

N-acetyl-D-galactosamine (72-87-7,1136-42-1,1136-44-3,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4,6082-29-7) → methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside (176691-04-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / dowex 50W-X₈ (H+ form) / 24 h / Heating

2: 85 percent / pyridine / 2 h / -60 °C

3: pyridine / CH₂Cl₂ / 2 h / 0 °C

4: 63 percent / cysteamine, dithioerythritol / dimethylformamide / 20 h / 20 °C

With pyridine; 1,4-dithio-erythritol; Dowex 50W-X₈ (H+ form); Cysteamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/P19960000581

Reference yield:

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride (51224-18-1) → methyl 2-acetamido-S-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-3,6-di-O-benzoyl-2-deoxy-4-thio-α-D-glucopyranoside (176691-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / sodium sulfite / H₂O; acetone / 0.33 h / Ambient temperature

2: 63 percent / cysteamine, dithioerythritol / dimethylformamide / 20 h / 20 °C

With 1,4-dithio-erythritol; Cysteamine; sodium sulfite; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1039/P19960000581

upstream raw materials:

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranose

methyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-trifluoromethanesulfonyl-β-D-galactopyranoside

N-acetyl-D-galactosamine

S-thiouronium 2-N-acetamido-3,4,6-tri-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside hydrochloride