(3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester
• CAS No.: 158585-07-0
• Molecular Formula: C₇₁H₆₂N₂O₁₂
• Molecular Weight: 1135.28
• Mol file: 158585-07-0.mol

Synonyms:(3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

Chemical Property of (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester

There total 37 articles about (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester 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: 79.0%

4-(6-Benzyloxy-2-(benzyloxycarbonyl)benzoyl)-3,5-dibenzyloxybenzoic Acid (158585-06-9) + 4-hydroxy-3-[4-(phenylmethoxy)benzoylamino]-1-(phenylmethoxycarbonyl)-hexahydroazepine (158584-98-6) → (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester (158585-07-0)

Guidance literature:

With dmap; 2-chloro-1-methyl-pyridinium iodide; triethylamine; In dichloromethane; at 25 ℃; for 5h;

DOI:10.1021/ja00097a072

Reference yield:

[(1R,2R)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-pent-4-enyl]-carbamic acid tert-butyl ester (158584-92-0) → (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester (158585-07-0)

Guidance literature:

Multi-step reaction with 12 steps

1: CSA / CH₂Cl₂ / 3 h / 25 °C

2: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, 20 h, 2.) MeOH, 25 deg C, 5 h

3: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

4: NaN₃ / dimethylformamide / 24 h / 25 °C

5: H₂ / 10percent Pd/C / tetrahydrofuran / 19 h / 25 °C

6: 3 N aq. NaOH / dioxane / 0.25 h / 0 °C

7: 96 percent / TBAF / tetrahydrofuran / 16 h / 25 °C

8: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

9: t-BuOK / tetrahydrofuran / 0.17 h / 25 °C

10: TFA / CH₂Cl₂ / 1 h / 25 °C

11: Et₃N / CH₂Cl₂ / 1.5 h / 25 °C

12: 79 percent / 2-chloro-1-methylpyridinium iodide, Et₃N, DMAP / CH₂Cl₂ / 3.5 h / 25 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; hydrogen; dihydrogen peroxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

(4R,5R)-5-Allyl-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (171564-49-1) → (3R,4R)-3-(4-Benzyloxy-benzoylamino)-4-[3,5-bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoyloxy]-azepane-1-carboxylic acid benzyl ester (158585-07-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) 9-BBN, 2.) 3 N aq. NaOH, 30percent H₂O₂ / 1.) THF, 25 deg C, 20 h, 2.) MeOH, 25 deg C, 5 h

2: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3: NaN₃ / dimethylformamide / 24 h / 25 °C

4: H₂ / 10percent Pd/C / tetrahydrofuran / 19 h / 25 °C

5: 3 N aq. NaOH / dioxane / 0.25 h / 0 °C

6: 96 percent / TBAF / tetrahydrofuran / 16 h / 25 °C

7: Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

8: t-BuOK / tetrahydrofuran / 0.17 h / 25 °C

9: TFA / CH₂Cl₂ / 1 h / 25 °C

10: Et₃N / CH₂Cl₂ / 1.5 h / 25 °C

11: 79 percent / 2-chloro-1-methylpyridinium iodide, Et₃N, DMAP / CH₂Cl₂ / 3.5 h / 25 °C

With dmap; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; sodium azide; potassium tert-butylate; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; hydrogen; dihydrogen peroxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-(6-Benzyloxy-2-(benzyloxycarbonyl)benzoyl)-3,5-dibenzyloxybenzoic Acid

4-hydroxy-3-[4-(phenylmethoxy)benzoylamino]-1-(phenylmethoxycarbonyl)-hexahydroazepine

4-(benzyloxy)benzoic acid chloride

benzyl bromide