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

Base Information

• Chemical Name: (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid
• CAS No.: 264197-96-8
• Molecular Formula: C₂₂H₃₂N₂O₇
• Molecular Weight: 436.505

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

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

There total 7 articles about (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid 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:

[(S)-4-Benzyloxycarbonylamino-4-((R)-5-formyl-tetrahydro-furan-2-yl)-butyl]-carbamic acid tert-butyl ester (264197-97-9) → (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid (264197-96-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In tert-butyl alcohol; at 20 ℃; for 12h;

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) → (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid (264197-96-8)

Guidance literature:

Multi-step reaction with 7 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

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; pyridinium p-toluenesulfonate; L-Selectride; magnesium; dimethyl sulfoxide; triethylamine; 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;

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) → (2RS,5R,1'S)-5-(1'-Benzyloxycarbonylamino-4'-tert-butoxycarbonylaminobutyl)tetrahydrofuran-2-carboxylic acid (264197-96-8)

Guidance literature:

Multi-step reaction with 6 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

With sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; pyridinium p-toluenesulfonate; L-Selectride; magnesium; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; dichloromethane; 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;

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

upstream raw materials:

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

Z-Orn(Boc)-OH

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

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

Downstream raw materials:

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

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

(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

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