(2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate

Base Information

• Chemical Name: (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate
• CAS No.: 264198-05-2
• Molecular Formula: C₃₄H₄₆N₄O₁₀
• Molecular Weight: 670.76

Synonyms:(2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate

Chemical Property of (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate

There total 8 articles about (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)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: 37.0%

methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride (35761-27-4,96192-93-7) + (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid (264197-96-8) → (2S,2'S,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate + (2S,2'R,5'R,1''S)-3-[5'-(1''-Benzyloxycarbonylamino-4''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-05-2)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 16h;

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''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-05-2)

Guidance literature:

Multi-step reaction with 8 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

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; diisopropyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; 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;

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''-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264198-05-2)

Guidance literature:

Multi-step reaction with 2 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

With sodium chlorite; sodium dihydrogenphosphate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; tert-butyl alcohol; 1: Oxidation / 2: Acylation;

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

upstream raw materials:

methyl (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoate hydrochloride

(2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid

Z-Orn(Boc)-OH

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

Downstream raw materials:

(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

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