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

Base Information

Chemical Name:(S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester
CAS No.:264197-83-3
Molecular Formula:C₂₂H₃₃N₅O₆
Molecular Weight:463.534
Hs Code.:

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

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

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

There total 12 articles about (S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester 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:

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

: 264197-84-4
(S)-2-Benzyloxycarbonylamino-3-{[(2R,5R)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

: 264197-83-3
(S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 4541-15-5
5-(benzyloxy)-1-pentanol

: 264197-83-3
(S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 12 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

12.1: TFA / CH₂Cl₂ / 2 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; trifluoroacetic acid; 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 / 12.1: Substitution;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z

Reference yield:

: 78999-24-3
5-benzyloxy-1-pentanal

: 264197-83-3
(S)-2-Benzyloxycarbonylamino-3-{[(2R,5S)-5-(4-guanidino-butyl)-tetrahydro-furan-2-carbonyl]-amino}-propionic acid methyl ester

Guidance literature:: Multi-step reaction with 11 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

11.1: TFA / CH₂Cl₂ / 2 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; trifluoroacetic acid; 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 / 11.1: Substitution;
DOI:10.1002/(SICI)1521-3765(20000218)6:4<666::AID-CHEM666>3.0.CO;2-Z