(2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Base Information

• Chemical Name: (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate
• CAS No.: 264198-00-7
• Molecular Formula: C₃₆H₅₈N₆O₁₂S
• Molecular Weight: 798.956

Synonyms:(2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Chemical Property of (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate

There total 9 articles about (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate 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:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate (264198-00-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N,N'-diisopropyl carbodiimide / CH₂Cl₂ / 4 h / 20 °C

2.1: Mg / diethyl ether / 1 h / Heating

2.2: LiCl; CuCN / tetrahydrofuran / 0.25 h / -40 °C

2.3: 3.72 g / tetrahydrofuran / 0.67 h / -78 - -5 °C

3.1: 46 percent / L-Selectride / tetrahydrofuran / 1 h / -100 - -70 °C

4.1: MCPBA / CH₂Cl₂ / 3.5 h / 20 °C

5.1: 670 mg / PPTS / CH₂Cl₂ / 12 h / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -60 - 0 °C

7.1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

8.1: 61 percent / iPr₂NEt; EDC; HOBt / tetrahydrofuran / 18 h / 20 °C

9.1: TFA / CH₂Cl₂ / 4 h / 20 °C

10.1: Et₃N; HgCl₂ / dimethylformamide / 2.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; pyridinium p-toluenesulfonate; L-Selectride; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Esterification / 2.1: Metallation / 2.2: Substitution / 2.3: Acylation / 3.1: Reduction / 4.1: Epoxidation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Oxidation / 8.1: Acylation / 9.1: Deacylation / 10.1: Substitution;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

[(S)-4-Benzyloxycarbonylamino-4-((R)-5-formyl-tetrahydro-furan-2-yl)-butyl]-carbamic acid tert-butyl ester (264197-97-9) → (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate (264198-00-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

2: 61 percent / iPr₂NEt; EDC; HOBt / tetrahydrofuran / 18 h / 20 °C

3: TFA / CH₂Cl₂ / 4 h / 20 °C

4: Et₃N; HgCl₂ / dimethylformamide / 2.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Oxidation / 2: Acylation / 3: Deacylation / 4: Substitution;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

2-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanethioic acid S-pyridin-2-yl ester (294664-65-6) → (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-butylsulfonylamino methyl propionate (264198-00-7)

Guidance literature:

Multi-step reaction with 9 steps

1.1: Mg / diethyl ether / 1 h / Heating

1.2: LiCl; CuCN / tetrahydrofuran / 0.25 h / -40 °C

1.3: 3.72 g / tetrahydrofuran / 0.67 h / -78 - -5 °C

2.1: 46 percent / L-Selectride / tetrahydrofuran / 1 h / -100 - -70 °C

3.1: MCPBA / CH₂Cl₂ / 3.5 h / 20 °C

4.1: 670 mg / PPTS / CH₂Cl₂ / 12 h / 20 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -60 - 0 °C

6.1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

7.1: 61 percent / iPr₂NEt; EDC; HOBt / tetrahydrofuran / 18 h / 20 °C

8.1: TFA / CH₂Cl₂ / 4 h / 20 °C

9.1: Et₃N; HgCl₂ / dimethylformamide / 2.5 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; pyridinium p-toluenesulfonate; L-Selectride; benzotriazol-1-ol; magnesium; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; mercury dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Metallation / 1.2: Substitution / 1.3: Acylation / 2.1: Reduction / 3.1: Epoxidation / 4.1: Ring cleavage / 5.1: Oxidation / 6.1: Oxidation / 7.1: Acylation / 8.1: Deacylation / 9.1: Substitution;

DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

upstream raw materials:

Z-Orn(Boc)-OH

[(S)-4-Benzyloxycarbonylamino-4-((R)-5-formyl-tetrahydro-furan-2-yl)-butyl]-carbamic acid tert-butyl ester

2-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentanethioic acid S-pyridin-2-yl ester

⁽⁴⁾-4-Benzyloxycarbonylamino-1-tert-butoxycarbonylamino-8-nonene-5-one

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