benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside
• CAS No.: 202464-70-8
• Molecular Formula: C₃₃H₃₇NO₁₀S
• Molecular Weight: 639.723
• Mol file: 202464-70-8.mol

Synonyms:benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Chemical Property of benzyl 2-acetamido-4,6-O-benzylidene-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-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

There total 6 articles about benzyl 2-acetamido-4,6-O-benzylidene-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: 96.0%

2-(phenylsulfonyl)ethanol (20611-21-6) + benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6) → benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (202464-70-8)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/ja973172d

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) → benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (202464-70-8)

Guidance literature:

Multi-step reaction with 2 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

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

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-4,6-O-benzylidene-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (202464-70-8)

Guidance literature:

Multi-step reaction with 4 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

With 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; N,N-dimethyl-formamide;

DOI:10.1135/cccc20051615

upstream raw materials:

2-(phenylsulfonyl)ethanol

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

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

N-Acetyl-D-glucosamine

Downstream raw materials:

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

N-acetyl-α-D-muramic acid, 4,6-diacetate, 1-(benzyl hexadecyl phosphate)

N-acetyl-4-O-(3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-β-D-glucopyranosyl)-α-D-muramic acid, 6-acetate, 1-(benzyl hexadecyl phosphate)

C₄₈H₇₈N₃O₁₇P