(S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester

Base Information

• Chemical Name: (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester
• CAS No.: 187395-94-4
• Molecular Formula: C₂₂H₃₃NO₆
• Molecular Weight: 407.507
• Mol file: 187395-94-4.mol

Synonyms:(S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester

Chemical Property of (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester

There total 5 articles about (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl 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: 55.0%

(S)-9-Benzyloxycarbonylamino-10-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-10-oxo-decanoic acid tert-butyl ester (187396-20-9) → (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester (187395-94-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1021/jm9603072

Reference yield:

8-bromooctanoic acid (17696-11-6) → (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester (187395-94-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / H₂SO₄ / diethyl ether

2: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -55 deg C, b) RT, 16 h

3: 10percent aq. citric acid / tetrahydrofuran / 48 h

4: 99 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

5: 55 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; sulfuric acid; triethylamine; citric acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/jm9603072

Reference yield:

8-bromo-octanoic acid tert-butyl ester (77383-17-6) → (S)-2-Benzyloxycarbonylamino-decanedioic acid 10-tert-butyl ester (187395-94-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) HMPA / 1.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, a) -55 deg C, b) RT, 16 h

2: 10percent aq. citric acid / tetrahydrofuran / 48 h

3: 99 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

4: 55 percent / 0.5 N aq. LiOH / tetrahydrofuran / 4 h / Ambient temperature

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; n-butyllithium; triethylamine; citric acid; In tetrahydrofuran;

DOI:10.1021/jm9603072

upstream raw materials:

(S)-9-Benzyloxycarbonylamino-10-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-10-oxo-decanoic acid tert-butyl ester

8-bromooctanoic acid

8-bromo-octanoic acid tert-butyl ester

(S)-9-Amino-10-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-10-oxo-decanoic acid tert-butyl ester

Downstream raw materials:

(S)-9-Benzyloxycarbonylamino-9-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

(S)-9-Amino-9-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester

(S)-N-((S)-1-Carbamoyl-2-phenyl-ethyl)-3-{[(2R,5S)-2-(1H-indol-3-ylmethyl)-2-methyl-3,13-dioxo-1,4-diaza-cyclotridecane-5-carbonyl]-amino}-succinamic acid cyclohexyl ester

(S)-9-[(R)-2-tert-Butoxycarbonylamino-3-(1H-indol-3-yl)-2-methyl-propionylamino]-9-[(S)-1-((S)-1-carbamoyl-2-phenyl-ethylcarbamoyl)-2-cyclohexyloxycarbonyl-ethylcarbamoyl]-nonanoic acid tert-butyl ester