benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Base Information

• Chemical Name: benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside
• CAS No.: 917029-93-7
• Molecular Formula: C₄₂H₅₄N₂O₁₉S
• Molecular Weight: 922.959
• Mol file: 917029-93-7.mol

Synonyms:benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

Chemical Property of benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-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 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

There total 16 articles about benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-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: 65.0%

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonylamino]-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-92-6) + acetic anhydride (108-24-7) → benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-93-7)

Guidance literature:

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonylamino]-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside; With zinc(II) chloride; In acetic acid;

acetic anhydride; With zinc; In tetrahydrofuran; acetic acid;

DOI:10.1021/ja302099u

Reference yield:

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (914642-50-5) → benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-93-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 55 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂

2: ZnCl₂; AcOH

3: 2.1 g / AcOH; Zn / tetrahydrofuran

With 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; zinc(II) chloride; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1135/cccc20051615

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) → benzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (917029-93-7)

Guidance literature:

Multi-step reaction with 6 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: 91 percent / triflic acid; triethylsilane / CH₂Cl₂ / 1 h / -78 °C

4.1: 55 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂

5.1: ZnCl₂; AcOH

6.1: 2.1 g / AcOH; Zn / tetrahydrofuran

With triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium hydride; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc(II) chloride; zinc; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1135/cccc20051615

upstream raw materials:

acetic anhydride

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

benzyl 3,4,6-tri-O-acetyl-2-deoxy-2-[(2,2,2-trichloroethoxy)carbonylamino]-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-benzyl-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

Downstream raw materials:

(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-phosphonooxy-tetrahydro-pyran-4-yloxy]-propionic acid 2-benzenesulfonyl-ethyl ester

dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[N-hydroxysuccinimidyloxy)carbonyl]ethyl}-α-D-glucopyranosyl phosphate

dibenzyl 3,4,6-tri-O-acethyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranosyl phosphate

dibenzyl 3,4,6-tri-O-acetyl-2-deoxy-2-acetamido-β-D-glucopyranosyl-(1->4)-2-acetamido-6-O-acetyl-2-deoxy-3-O-(D-2-propionyl-L-alanyl-D-glutamic diamide)-α-D-glucopyranosyl phosphate