(2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate

Base Information

• Chemical Name: (2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate
• CAS No.: 294664-68-9
• Molecular Formula: C₃₂H₄₉N₅O₁₀
• Molecular Weight: 663.769
• Mol file: 294664-68-9.mol

Synonyms:(2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate

Chemical Property of (2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate

There total 11 articles about (2S,2'R,5'RS)-3-(5'-{4''-[N¹''',N²'''-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: 78.0%

tert-butyl N-[amino(tert-butoxycarbonylamino)methylene]carbamate (332882-82-3,154476-57-0) + (2S,2'R,5'RS)-3-[5'-(4''-Hydroxybutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate (264197-81-1) → (2S,2'R,5'RS)-3-(5'-{4''-[N1''',N2'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate (294664-68-9)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; 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:

5-(benzyloxy)-1-pentanol (4541-15-5) → (2S,2'R,5'RS)-3-(5'-{4''-[N1''',N2'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate (294664-68-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 98 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -60 - 0 °C

2.1: Mg / tetrahydrofuran / 1 h / 20 °C

2.2: 80 percent / tetrahydrofuran / 0.33 h / 20 °C

3.1: 90 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

4.1: pyridine / CH₂Cl₂ / 36 h / 0 °C

5.1: K₂CO₃ / methanol / 2 h / 20 °C

6.1: 188 mg / AcOH / CH₂Cl₂ / 2 h / 20 °C

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

8.1: 3.37 g / aq. NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; various solvent(s) / 12 h / 20 °C

9.1: 93 percent / H₂; 10 percent Pd/C / tetrahydrofuran; aq. methanol / 18 h / 20 °C

10.1: 2.20 g / BOP; Et₃N / acetonitrile / 16 h / 20 °C

11.1: 78 percent / PPh₃; DIAD / tetrahydrofuran / 16 h / 20 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; palladium on activated charcoal; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Oxidation / 2.1: Metallation / 2.2: Grignard reaction / 3.1: Hydrolysis / 4.1: Substitution / 5.1: Cyclization / 6.1: Ring cleavage / 7.1: Oxidation / 8.1: Oxidation / 9.1: Hydrogenolysis / 10.1: Acylation / 11.1: Substitution;

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

Reference yield:

5-benzyloxy-1-pentanal (78999-24-3) → (2S,2'R,5'RS)-3-(5'-{4''-[N1''',N2'''-Bis(tert-butoxycarbonyl)guanidino]butyl}tetrahydrofuran-2'-carbamoyl)-2-benzyloxycarbonylamino methyl propionate (294664-68-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Mg / tetrahydrofuran / 1 h / 20 °C

1.2: 80 percent / tetrahydrofuran / 0.33 h / 20 °C

2.1: 90 percent / aq. HCl / tetrahydrofuran / 2 h / 20 °C

3.1: pyridine / CH₂Cl₂ / 36 h / 0 °C

4.1: K₂CO₃ / methanol / 2 h / 20 °C

5.1: 188 mg / AcOH / CH₂Cl₂ / 2 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: 93 percent / H₂; 10 percent Pd/C / tetrahydrofuran; aq. methanol / 18 h / 20 °C

9.1: 2.20 g / BOP; Et₃N / acetonitrile / 16 h / 20 °C

10.1: 78 percent / PPh₃; DIAD / tetrahydrofuran / 16 h / 20 °C

With pyridine; hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; palladium on activated charcoal; oxalyl dichloride; di-isopropyl azodicarboxylate; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; acetonitrile; tert-butyl alcohol; 1.1: Metallation / 1.2: Grignard reaction / 2.1: Hydrolysis / 3.1: Substitution / 4.1: Cyclization / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Oxidation / 8.1: Hydrogenolysis / 9.1: Acylation / 10.1: Substitution;

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

upstream raw materials:

tert-butyl N-[amino(tert-butoxycarbonylamino)methylene]carbamate

(2S,2'R,5'RS)-3-[5'-(4''-Hydroxybutyl)tetrahydrofuran-2'-carbamoyl]-2-benzyloxycarbonylamino methyl propionate

5-(benzyloxy)-1-pentanol

5-benzyloxy-1-pentanal

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-{[(2R,5R)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

(S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

Refernces