(8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester

Base Information

• Chemical Name: (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester
• CAS No.: 289913-46-8
• Molecular Formula: C₂₄H₃₃N₃O₆S
• Molecular Weight: 491.609
• Mol file: 289913-46-8.mol

Synonyms:

Chemical Property of (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester

There total 6 articles about (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl 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:

(R)-2-({1-[2-((S)-2-Benzyloxycarbonylamino-4-bromo-butyrylamino)-ethyl]-cyclopentanecarbonyl}-amino)-3-mercapto-propionic acid methyl ester → (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester (289913-46-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran;

DOI:10.1016/S0960-894X(00)00175-X

Reference yield:

1-(2-azido-ethyl)-cyclopentanecarboxylic acid (220875-87-6) → (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester (289913-46-8)

Guidance literature:

Multi-step reaction with 6 steps

1: HBTU; DIEA / dimethylformamide

2: Me₃P; H₂O / tetrahydrofuran

3: pyridine / 80 °C

4: CBr₄; Ph₃P / CH₂Cl₂

5: TFA; Et₃SiH

6: DBU / tetrahydrofuran

With pyridine; triethylsilane; carbon tetrabromide; water; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; trimethylphosphane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: Condensation / 2: Reduction / 3: Addition / 4: Bromination / 5: acidolysis / 6: Cyclization;

DOI:10.1016/S0960-894X(00)00175-X

Reference yield:

(R)-2-{[1-(2-Amino-ethyl)-cyclopentanecarbonyl]-amino}-3-tritylsulfanyl-propionic acid methyl ester → (8R,13S)-13-Benzyloxycarbonylamino-6,14-dioxo-10-thia-7,15-diaza-spiro[4.12]heptadecane-8-carboxylic acid methyl ester (289913-46-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 80 °C

2: CBr₄; Ph₃P / CH₂Cl₂

3: TFA; Et₃SiH

4: DBU / tetrahydrofuran

With pyridine; triethylsilane; carbon tetrabromide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; 1: Addition / 2: Bromination / 3: acidolysis / 4: Cyclization;

DOI:10.1016/S0960-894X(00)00175-X

upstream raw materials:

1-(2-azido-ethyl)-cyclopentanecarboxylic acid

(R)-2-{[1-(2-Azido-ethyl)-cyclopentanecarbonyl]-amino}-3-tritylsulfanyl-propionic acid methyl ester

(R)-2-({1-[2-((S)-2-Benzyloxycarbonylamino-4-hydroxy-butyrylamino)-ethyl]-cyclopentanecarbonyl}-amino)-3-tritylsulfanyl-propionic acid methyl ester