benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside
• CAS No.: 917029-91-5
• Molecular Formula: C₂₈H₃₅NO₁₁S
• Molecular Weight: 593.652
• Mol file: 917029-91-5.mol

Synonyms:benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

There total 7 articles about benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-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: 87.0%

acetyl chloride (75-36-5) + benzyl 2-acetamido-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-90-4) → benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-91-5)

Guidance literature:

With pyridine; In dichloromethane; at -30 - 0 ℃;

DOI:10.1135/cccc20051615

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) → benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-91-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dioxane / 2 h / 95 °C

1.2: 80 percent / dioxane / 3 h / 60 °C

2.1: 84 percent / DMAP; EDCl / CH₂Cl₂

3.1: 94 percent / acetic acid; H₂O / 1.5 h / 60 °C

4.1: 87 percent / pyridine / CH₂Cl₂ / -30 - 0 °C

With pyridine; dmap; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water; acetic acid;

DOI:10.1135/cccc20051615

Reference yield:

N-Acetyl-D-glucosamine (7512-17-6,72-87-7,1136-42-1,1136-44-3,6082-29-7,6730-06-9,7772-94-3,10036-64-3,14131-60-3,14131-64-7,14131-68-1,14215-68-0,62057-49-2,62057-50-5,62057-51-6,62057-52-7,62057-53-8,62057-54-9,62057-55-0,62057-56-1,62075-50-7,62137-54-6,134451-97-1,134522-12-6,148347-16-4) → benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-91-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 70 percent / AcCl / CH₂Cl₂ / 4 h / 75 °C

2.1: 95 percent / p-toluenesulfonic acid; triethyl ortoformate / dimethylformamide; dioxane / 20 h / 20 °C

3.1: NaH / dioxane / 2 h / 95 °C

3.2: 80 percent / dioxane / 3 h / 60 °C

4.1: 84 percent / DMAP; EDCl / CH₂Cl₂

5.1: 94 percent / acetic acid; H₂O / 1.5 h / 60 °C

6.1: 87 percent / pyridine / CH₂Cl₂ / -30 - 0 °C

With pyridine; dmap; sodium hydride; toluene-4-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; acetyl chloride; orthoformic acid triethyl ester; In 1,4-dioxane; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1135/cccc20051615

upstream raw materials:

acetyl chloride

benzyl 2-acetamido-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

N-Acetyl-D-glucosamine