(8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane

Base Information

• Chemical Name: (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane
• CAS No.: 134848-65-0
• Molecular Formula: C₃₁H₄₆N₄O₈
• Molecular Weight: 602.728

Synonyms:(8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane

Chemical Property of (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane

Chemical Property:

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Technology Process of (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane

There total 7 articles about (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane 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-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (8S,11S,12R)-8-Amino-11-cyclohexylmethyl-12-hydroxy-1-oxa-4,10-diaza-cyclotridecane-5,9,13-trione → (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane (134848-65-0)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20 ℃; Yield given;

DOI:10.1021/jm00113a005

Reference yield:

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt (34897-61-5) → (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane (134848-65-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / hydrobenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

2: 97 percent / 4-(dimethylamino)pyridine (DMAP), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 °C

3: TFA / CH₂Cl₂ / Ambient temperature

4: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

5: TFA, Me₂S / Ambient temperature

6: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

With dmap; dimethylsulfide; diphenyl phosphoryl azide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a005

Reference yield:

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid (121533-54-8) → (8S,11S,12R)-11-(cyclohexylmethyl)-8-<-L-phenylalanyl>amino>-12-hydroxy-5,9,13-trioxo-1-oxa-4,10-diazacyclotridecane (134848-65-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / 4-(dimethylamino)pyridine (DMAP), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 °C

2: TFA / CH₂Cl₂ / Ambient temperature

3: diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

4: TFA, Me₂S / Ambient temperature

5: hydroxybenzotriazole monohydrate (HOBt), 1-<3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride (EDC) / CH₂Cl₂ / 0 - 20 °C

With dmap; dimethylsulfide; diphenyl phosphoryl azide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm00113a005

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

N-(benzyloxycarbonyl)-L-glutamic acid α-t-butyl ester dicyclohexylamine salt

(4S,5R)-3-tert-Butoxycarbonyl-4-cyclohexyl-methyl-2,2-dimethyloxazolidine-5-carboxylic acid

Z-Glu(2-hydroxyethyl)-OtBu

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