(4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 119961-33-0
• Molecular Formula: C₃₃H₄₆N₄O₈
• Molecular Weight: 626.75
• Mol file: 119961-33-0.mol

Synonyms:

Chemical Property of (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 25 articles about (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl 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:

Boc-Ala-H (79069-50-4) → (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (119961-33-0,120052-38-2,131903-25-8,131903-26-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 40.9 percent / tris(6,6,7,7,8,8,8-heptafluoro-2,2-dimethyloctane-3,5-dionato)europium(III) / CH₂Cl₂ / 16 h / 5 - 8 °C

2: 72.2 percent / ammonium acetate / molecular sieves 4 Angstroem / CHCl₃ / 3 h / Heating

3: 1.) H₂, H₃PO₄, 2.) NaHCO₃ / 1.) 5percent Pt/C / 1.) THF, r.t., 2.) water, THF, r.t., 3 h

4: diisopropylethylamine / 16 h / Ambient temperature; further base: MeONa

5: pyridinium toluene-p-sulphonate / CH₂Cl₂ / 24 h / Ambient temperature

6: 1.) aq. NaOH, 2.) N-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) MeOH, THF, r.t., 3-5 h, 2.) THF, r.t., 16 h

With ammonium acetate; sodium hydroxide; phosphoric acid; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; platinum on activated charcoal; tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III); 4 A molecular sieve; In dichloromethane; chloroform;

Reference yield:

(6S)-6-<(1S)-1-(tert-butoxycarbonylamino)ethyl>-5,6-dihydro-2H-pyran-2,4(3H)-dione (119960-20-2) → (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (119961-33-0,120052-38-2,131903-25-8,131903-26-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 72.2 percent / ammonium acetate / molecular sieves 4 Angstroem / CHCl₃ / 3 h / Heating

2: 1.) H₂, H₃PO₄, 2.) NaHCO₃ / 1.) 5percent Pt/C / 1.) THF, r.t., 2.) water, THF, r.t., 3 h

3: diisopropylethylamine / 16 h / Ambient temperature; further base: MeONa

4: pyridinium toluene-p-sulphonate / CH₂Cl₂ / 24 h / Ambient temperature

5: 1.) aq. NaOH, 2.) N-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) MeOH, THF, r.t., 3-5 h, 2.) THF, r.t., 16 h

With ammonium acetate; sodium hydroxide; phosphoric acid; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; platinum on activated charcoal; 4 A molecular sieve; In dichloromethane; chloroform;

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (4S,5S)-5-[(S)-2-Benzyloxycarbonylamino-3-(N'-benzyloxycarbonylmethyl-N'-methyl-hydrazinocarbonyl)-propyl]-2,2,4-trimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (119961-33-0,120052-38-2,131903-25-8,131903-26-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) H₂, H₃PO₄, 2.) NaHCO₃ / 1.) 5percent Pt/C / 1.) THF, r.t., 2.) water, THF, r.t., 3 h

2: diisopropylethylamine / 16 h / Ambient temperature; further base: MeONa

3: pyridinium toluene-p-sulphonate / CH₂Cl₂ / 24 h / Ambient temperature

4: 1.) aq. NaOH, 2.) N-hydroxybenzotriazole (HOBT), 1,3-dicyclohexylcarbodiimide (DCC) / 1.) MeOH, THF, r.t., 3-5 h, 2.) THF, r.t., 16 h

With sodium hydroxide; phosphoric acid; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; platinum on activated charcoal; In dichloromethane;

upstream raw materials:

benzyl 2-(1-methylhydrazinyl)acetate

(6R)-6-<(1R)-1-(tert-butoxycarbonylamino)ethyl>-5,6-dihydro-2H-pyran-2,4(3H)-dione

((R)-1-{(R)-4-[(Z)-Hydroxyimino]-6-oxo-tetrahydro-pyran-2-yl}-ethyl)-carbamic acid tert-butyl ester

(4R,6R)-4-benzyloxycarbonylamino-6-<(1R)-1-(tert-butoxycarbonylamino)ethyl>tetrahydropyran-2-one