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

Base Information

• Chemical Name: 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
• CAS No.: 917030-02-5
• Molecular Formula: C₄₉H₆₇N₆O₂₂P
• Molecular Weight: 1123.07

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 21 articles about 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 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:

benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside (914642-50-5) → 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 (917030-02-5)

Guidance literature:

Multi-step reaction with 9 steps

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

2: ZnCl₂; AcOH

3: 2.1 g / AcOH; Zn / tetrahydrofuran

4: 92 percent / H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 20 °C

5: tetrazole / acetonitrile / 4 h / 20 °C

6: 1.5 g / aq. hydrogen peroxide / tetrahydrofuran / 2 h / -80 - 20 °C

7: DBU / CH₂Cl₂ / 0.5 h / 0 °C

8: 577 mg / EDCl / dimethylformamide / 20 °C

9: 120.95 mg / N,N'-diisopropylethylamine / dimethylformamide / 24 h / 20 °C

With 1H-tetrazole; 4 A molecular sieve; hydrogen; dihydrogen peroxide; silver trifluoromethanesulfonate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1135/cccc20051615

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside (78246-81-8) → 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 (917030-02-5)

Guidance literature:

Multi-step reaction with 12 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

7.1: 92 percent / H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 20 °C

8.1: tetrazole / acetonitrile / 4 h / 20 °C

9.1: 1.5 g / aq. hydrogen peroxide / tetrahydrofuran / 2 h / -80 - 20 °C

10.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

11.1: 577 mg / EDCl / dimethylformamide / 20 °C

12.1: 120.95 mg / N,N'-diisopropylethylamine / dimethylformamide / 24 h / 20 °C

With 1H-tetrazole; triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; dihydrogen peroxide; silver trifluoromethanesulfonate; sodium hydride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc(II) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

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) → 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 (917030-02-5)

Guidance literature:

Multi-step reaction with 14 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: 91 percent / triflic acid; triethylsilane / CH₂Cl₂ / 1 h / -78 °C

6.1: 55 percent / 4 Angstroem molecular sieves; AgOTf / CH₂Cl₂

7.1: ZnCl₂; AcOH

8.1: 2.1 g / AcOH; Zn / tetrahydrofuran

9.1: 92 percent / H₂ / Pd/C / tetrahydrofuran; methanol / 2 h / 20 °C

10.1: tetrazole / acetonitrile / 4 h / 20 °C

11.1: 1.5 g / aq. hydrogen peroxide / tetrahydrofuran / 2 h / -80 - 20 °C

12.1: DBU / CH₂Cl₂ / 0.5 h / 0 °C

13.1: 577 mg / EDCl / dimethylformamide / 20 °C

14.1: 120.95 mg / N,N'-diisopropylethylamine / dimethylformamide / 24 h / 20 °C

With 1H-tetrazole; triethylsilane; dmap; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; dihydrogen peroxide; silver trifluoromethanesulfonate; sodium hydride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; acetyl chloride; orthoformic acid triethyl ester; zinc(II) chloride; zinc; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1135/cccc20051615

upstream raw materials:

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

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

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

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

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