(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

Base Information

Chemical Name:(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane
CAS No.:134848-71-8
Molecular Formula:C₃₂H₅₀N₄O₇
Molecular Weight:602.772
Hs Code.:

(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<<N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

Synonyms:(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

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Chemical Property of (3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

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Technology Process of (3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

There total 14 articles about (3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-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:

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

: 134848-71-8
(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

Guidance literature:: Multi-step reaction with 5 steps

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

2: 56 percent / H₂, AcOH / 10percent Pd/C / methanol; tetrahydrofuran / 2068.6 Torr

3: 34 percent / 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; dimethylformamide / 0 - 20 °C

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

Reference yield:

: (2S,3R)-2-Amino-7-azido-1-cyclohexyl-3-hydroxy-heptan-4-one

: 134848-71-8
(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

Guidance literature:: Multi-step reaction with 8 steps

1: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

2: 44 percent / NaBH₄ / methanol / 0.25 h / 0 °C

3: TFA / CH₂Cl₂ / Ambient temperature

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

5: 56 percent / H₂, AcOH / 10percent Pd/C / methanol; tetrahydrofuran / 2068.6 Torr

6: 34 percent / diphenyl phosphorazidate (DPPA), Et₃N / dimethylformamide / 1.) 0 deg C, 2.) 7.5 deg C, 3 d, 3.) RT, 16 h

7: TFA / CH₂Cl₂ / Ambient temperature

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

With sodium tetrahydroborate; 1-Hydrobenzotriazole monohydrate; diphenyl phosphoryl azide; hydrogen; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; 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

: 134848-71-8
(3S,11S,12R,13S)-13-(cyclohexylmethyl)-11,12-dihydroxy-3-<-L-phenylalanyl>amino>-2,6-dioxo-1,7-diazacyclotridecane

Guidance literature:: Multi-step reaction with 9 steps

1: 1 N aq. HCl / 60 - 65 °C

2: NaHCO₃ / tetrahydrofuran; H₂O / 4 °C

3: 44 percent / NaBH₄ / methanol / 0.25 h / 0 °C

4: TFA / CH₂Cl₂ / Ambient temperature

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

6: 56 percent / H₂, AcOH / 10percent Pd/C / methanol; tetrahydrofuran / 2068.6 Torr

7: 34 percent / 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; dimethylformamide / 0 - 20 °C

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