<3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester

Base Information

• Chemical Name: <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester
• CAS No.: 111437-55-9
• Molecular Formula: C₄₅H₇₂N₈O₉
• Molecular Weight: 869.115

Synonyms:<3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester

Chemical Property of <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester

There total 18 articles about <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl 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:

N-(benzyloxycarbonyl)-O-allyl-L-serinol (111437-57-1) → <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester (111437-55-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 91 percent / (iPr)2NEt / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to room temperature

2: 91 percent / 9-BBN / tetrahydrofuran / 1.) 0 deg C to room temperature, 2.) room temperature, 5 h

3: 75 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.5 h

4: 810 mg / NaH / tetrahydrofuran / 0.17 h / 0 °C

5: 1.) H₂, 2.) N-(benzyloxy)succinimide / 1.) Pd/C / 1.) methanol, 2.) CH₂Cl₂, room temperature

6: 1.02 g / DIBAH / tetrahydrofuran; hexane / 0 °C

7: 0.90 g / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂

8: 1.) sodium acetate, 2.) sodium cyanoborohydride / 1.) 0 deg C, 30 min, 2.) -20 deg C to room temperature

9: CHCl₃ / 12 h / Ambient temperature

10: aq. LiOH / dioxane / 2 h / Ambient temperature

11: dicyclohexylcarbodiimide / ethyl acetate / 0.5 h / 0 °C

12: H₂, 4-pyrrolidinopyridine / Pd/C / ethanol; dioxane / 4.5 h / 90 °C

13: 1.) conc. HCl, 2.) Et₃N / 1.) methanol, 60 deg C, 3.5 h, 2.) CHCl₃, room temperature

14: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h

15: 2.) NaOAc, NaCNBH₃ / 1.) 2-propanol, 2.) 0 deg C, 2 h, room temperature

16: H₂ / Pd/C / methanol / 0.5 h

17: Et₃N, HOBt, DCC / dimethylformamide / 1.) 0 deg C, 4 h, 2.) room temperature

With hydrogenchloride; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 1-(benzyloxy)pyrrolidine-2,5-dione; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; benzotriazol-1-ol; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00397a003

Reference yield:

N-(benzyloxycarbonyl)-O-allyl-L-serine methyl ester (111437-56-0) → <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester (111437-55-9)

Guidance literature:

Multi-step reaction with 18 steps

1: 82 percent / DIBAH / tetrahydrofuran; hexane / 0.33 h / 0 °C

2: 91 percent / (iPr)2NEt / CH₂Cl₂ / 1.) 0 deg C, 10 min, 2.) 0 deg C to room temperature

3: 91 percent / 9-BBN / tetrahydrofuran / 1.) 0 deg C to room temperature, 2.) room temperature, 5 h

4: 75 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.5 h

5: 810 mg / NaH / tetrahydrofuran / 0.17 h / 0 °C

6: 1.) H₂, 2.) N-(benzyloxy)succinimide / 1.) Pd/C / 1.) methanol, 2.) CH₂Cl₂, room temperature

7: 1.02 g / DIBAH / tetrahydrofuran; hexane / 0 °C

8: 0.90 g / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂

9: 1.) sodium acetate, 2.) sodium cyanoborohydride / 1.) 0 deg C, 30 min, 2.) -20 deg C to room temperature

10: CHCl₃ / 12 h / Ambient temperature

11: aq. LiOH / dioxane / 2 h / Ambient temperature

12: dicyclohexylcarbodiimide / ethyl acetate / 0.5 h / 0 °C

13: H₂, 4-pyrrolidinopyridine / Pd/C / ethanol; dioxane / 4.5 h / 90 °C

14: 1.) conc. HCl, 2.) Et₃N / 1.) methanol, 60 deg C, 3.5 h, 2.) CHCl₃, room temperature

15: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h

16: 2.) NaOAc, NaCNBH₃ / 1.) 2-propanol, 2.) 0 deg C, 2 h, room temperature

17: H₂ / Pd/C / methanol / 0.5 h

18: Et₃N, HOBt, DCC / dimethylformamide / 1.) 0 deg C, 4 h, 2.) room temperature

With hydrogenchloride; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 1-(benzyloxy)pyrrolidine-2,5-dione; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; benzotriazol-1-ol; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00397a003

Reference yield:

6(S)-<(benzyloxycarbonyl)amino>-4,8,10-trioxaundec-1-ene (111437-58-2) → <3R-<3R*,6S*,7(S*)>>-N-amino>-1-oxo-3-phenylpropyl>-6-methyl-5-oxo-1-oxa-4,7-diazacyclotetradec-3-yl>methyl>-L-valyl>-L-isoleucyl>-L-histidine methyl ester (111437-55-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 91 percent / 9-BBN / tetrahydrofuran / 1.) 0 deg C to room temperature, 2.) room temperature, 5 h

2: 75 percent / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂ / 0.5 h

3: 810 mg / NaH / tetrahydrofuran / 0.17 h / 0 °C

4: 1.) H₂, 2.) N-(benzyloxy)succinimide / 1.) Pd/C / 1.) methanol, 2.) CH₂Cl₂, room temperature

5: 1.02 g / DIBAH / tetrahydrofuran; hexane / 0 °C

6: 0.90 g / dimethyl sulfoxide, oxalyl chloride / CH₂Cl₂

7: 1.) sodium acetate, 2.) sodium cyanoborohydride / 1.) 0 deg C, 30 min, 2.) -20 deg C to room temperature

8: CHCl₃ / 12 h / Ambient temperature

9: aq. LiOH / dioxane / 2 h / Ambient temperature

10: dicyclohexylcarbodiimide / ethyl acetate / 0.5 h / 0 °C

11: H₂, 4-pyrrolidinopyridine / Pd/C / ethanol; dioxane / 4.5 h / 90 °C

12: 1.) conc. HCl, 2.) Et₃N / 1.) methanol, 60 deg C, 3.5 h, 2.) CHCl₃, room temperature

13: DMSO, oxalyl chloride / CH₂Cl₂ / 0.17 h

14: 2.) NaOAc, NaCNBH₃ / 1.) 2-propanol, 2.) 0 deg C, 2 h, room temperature

15: H₂ / Pd/C / methanol / 0.5 h

16: Et₃N, HOBt, DCC / dimethylformamide / 1.) 0 deg C, 4 h, 2.) room temperature

With hydrogenchloride; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; 1-(benzyloxy)pyrrolidine-2,5-dione; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; benzotriazol-1-ol; 4-pyrrolidin-1-ylpyridine; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00397a003

upstream raw materials:

(S)-2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-3-(1H-imidazol-4-yl)-propionic acid methyl ester; hydrochloride

N-(benzyloxycarbonyl)-O-allyl-L-serinol

N-(benzyloxycarbonyl)-O-allyl-L-serine methyl ester

6(S)-<(benzyloxycarbonyl)amino>-4,8,10-trioxaundec-1-ene

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