(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

Base Information

Chemical Name:(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal
CAS No.:134848-69-4
Molecular Formula:C₃₄H₅₂N₄O₈
Molecular Weight:644.809
Hs Code.:

(3S,12R,13S)-13-(cyclohexylmethyl)-3-<<N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

Synonyms:(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

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Chemical Property of (3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

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Technology Process of (3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

There total 10 articles about (3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal 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:

: 13574-13-5
Boc-Glu(OBzl)-OH

: 134848-69-4
(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

Guidance literature:: Multi-step reaction with 5 steps

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

2: 49 mg / H₂ / 10percent Pd/C / methanol / 2068.6 Torr

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

4: TFA / CH₂Cl₂ / Ambient temperature

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

With 1-Hydrobenzotriazole monohydrate; diphenyl phosphoryl azide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a005

Reference yield:

: 134848-99-0
(1R,2S)-2-Amino-1-[2-(3-azido-propyl)-[1,3]dioxolan-2-yl]-3-cyclohexyl-propan-1-ol

: 134848-69-4
(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

Guidance literature:: Multi-step reaction with 5 steps

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

2: 49 mg / H₂ / 10percent Pd/C / methanol / 2068.6 Torr

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

4: TFA / CH₂Cl₂ / Ambient temperature

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

With 1-Hydrobenzotriazole monohydrate; diphenyl phosphoryl azide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a005

Reference yield:

: 134848-98-9
3-[2-((4S,5R)-4-Cyclohexylmethyl-2-oxo-oxazolidin-5-yl)-[1,3]dioxolan-2-yl]-propionic acid

: 134848-69-4
(3S,12R,13S)-13-(cyclohexylmethyl)-3-<-L-phenylalanyl>amino>-12-hydroxy-2,6,11-trioxo-1,7-diazacyclotridecane ethylene glycol ketal

Guidance literature:: Multi-step reaction with 9 steps

1: 95 percent / BH₃*SMe₂ / tetrahydrofuran / 3 h / Ambient temperature

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: LiN₃ / dimethylformamide / Ambient temperature

4: 992 mg / Ba(OH)2 / dioxane; H₂O / Heating

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

6: 49 mg / H₂ / 10percent Pd/C / methanol / 2068.6 Torr

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

8: TFA / CH₂Cl₂ / Ambient temperature

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

With barium dihydroxide; lithium azide; dimethylsulfide borane complex; 1-Hydrobenzotriazole monohydrate; diphenyl phosphoryl azide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm00113a005