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

Base Information

• Chemical Name: (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate
• CAS No.: 264198-06-3
• Molecular Formula: C₄₀H₅₆N₆O₁₂
• Molecular Weight: 812.918

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 10 articles about (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N²''',N³'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino 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:

N,N'-bis-Boc-S-methyl-isothiourea (322474-21-5) + (S)-3-{[(2R,5R)-5-((S)-4-Amino-1-benzyloxycarbonylamino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-2-benzyloxycarbonylamino-propionic acid methyl ester → (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-06-3)

Guidance literature:

With triethylamine; mercury dichloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

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

Reference yield:

Z-Orn(Boc)-OH (7733-29-1,199924-46-4) → (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-06-3)

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: 37 percent / iPr₂NEt; HOBt; EDC / tetrahydrofuran / 16 h / 20 °C

9.1: TFA / CH₂Cl₂ / 2 h / 20 °C

10.1: 92 mg / Et₃N; HgCl₂ / dimethylformamide / 3 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'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-[N2''',N3'''-bis(tert-butoxycarbonyl)guanidino]butyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-06-3)

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: 37 percent / iPr₂NEt; HOBt; EDC / tetrahydrofuran / 16 h / 20 °C

3: TFA / CH₂Cl₂ / 2 h / 20 °C

4: 92 mg / Et₃N; HgCl₂ / dimethylformamide / 3 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

upstream raw materials:

N,N'-bis-Boc-S-methyl-isothiourea

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

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