(9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Base Information

• Chemical Name: (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane
• CAS No.: 143508-00-3
• Molecular Formula: C₃₆H₅₁Cl₃N₄O₁₁
• Molecular Weight: 822.18

Synonyms:

Chemical Property of (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

There total 13 articles about (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane 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:

2-(4-(benzyloxy)butyl)oxirane (133617-19-3,946390-77-8) → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (143508-00-3,143614-61-3)

Guidance literature:

Multi-step reaction with 13 steps

1: lithium azide / dimethylformamide

2: H₂ / Raney nickel / methanol

3: 87 percent / sodium bicarbonate / tetrahydrofuran; H₂O

4: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

5: H₂ / 10 percent Pd/C / methanol / 760 Torr

6: pyridinium dichromate (PDC) / dimethylformamide / 48 h

7: 45 percent / potassium carbonate / acetone / 6 h / Heating

8: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

9: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

10: H₂ / 10 percent Pd/C / methanol / 760 Torr

11: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

12: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

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

With 4-methyl-morpholine; dmap; dipyridinium dichromate; lithium azide; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00099a004

Reference yield:

1-Amino-6-benzyloxy-hexan-2-ol → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (143508-00-3,143614-61-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 87 percent / sodium bicarbonate / tetrahydrofuran; H₂O

2: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

3: H₂ / 10 percent Pd/C / methanol / 760 Torr

4: pyridinium dichromate (PDC) / dimethylformamide / 48 h

5: 45 percent / potassium carbonate / acetone / 6 h / Heating

6: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

7: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

8: H₂ / 10 percent Pd/C / methanol / 760 Torr

9: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

10: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

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

With 4-methyl-morpholine; dmap; dipyridinium dichromate; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00099a004

Reference yield:

1-Azido-6-benzyloxy-hexan-2-ol (143508-19-4) → (9S,12S,13R)-12-(cyclohexylmethyl)-9--L-phenylalanyl>-13-hydroxy-2-<<<(2,2,2-trichloroethoxy)carbonyl>amino>methyl>-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane (143508-00-3,143614-61-3)

Guidance literature:

Multi-step reaction with 12 steps

1: H₂ / Raney nickel / methanol

2: 87 percent / sodium bicarbonate / tetrahydrofuran; H₂O

3: 92 percent / 4-(dimethylamino)pyridine (DMAP), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / CH₂Cl₂ / 0 °C

4: H₂ / 10 percent Pd/C / methanol / 760 Torr

5: pyridinium dichromate (PDC) / dimethylformamide / 48 h

6: 45 percent / potassium carbonate / acetone / 6 h / Heating

7: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

8: hydroxybenzotriazole monohydrate (HOBt), 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC), N-methylmorpholine (NMM) / CH₂Cl₂ / 0 - 20 °C

9: H₂ / 10 percent Pd/C / methanol / 760 Torr

10: 4-(dimethylamino)pyridine (DMAP), 4-(dimethylamino)pyridine hydrochloride, 3-ethyl-1-<3-(dimethylamino)propyl>carbodiimide (EDC) / tetrahydrofuran; CHCl₃ / 19 h / Heating

11: trifluoroacetic acid (TFA) / CH₂Cl₂ / Ambient temperature

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

With 4-methyl-morpholine; dmap; dipyridinium dichromate; hydrogen; 4-(dimethylamino)pyridine hydrochloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; nickel; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jm00099a004

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

2-(4-(benzyloxy)butyl)oxirane

1-Azido-6-benzyloxy-hexan-2-ol

(6-Benzyloxy-2-hydroxy-hexyl)-carbamic acid 2,2,2-trichloro-ethyl ester

Downstream raw materials:

(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-dimethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

(9S,12S,13R)-12-(cyclohexylmethyl)-2-(N,N-diethylamino)-9--L-phenylalanyl>-13-hydroxy-6,10,14-trioxo-1,7-dioxa-11-azacyclotetradecane

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