(5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 84572-82-7
• Molecular Formula: C₂₈H₂₅N₂O₉P
• Molecular Weight: 564.488
• Mol file: 84572-82-7.mol

Synonyms:

Chemical Property of (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 14 articles about (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl 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:

diethyl 2-ethyl-3-oxoglutarate (16631-50-8) → (5R,6S)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (84572-82-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) NaBH₃CN, AcONH₄, 2) 6N HCl / 1) ethanol, 2) heating

2: MgO / H₂O

3: 1) H₂ / 1) Pd-C, 2) TsOH

4: 66 percent / CH₂Cl₂ / 10 h / Ambient temperature

5: AlCl₃ / various solvent(s) / 3 h / Ambient temperature

6: 1) N₂O₄, AcONa / 1) CHCl₃, 0 deg C, 1 hr, 2) CCl₄, reflux

7: 1) N₂O₂, CH₃COONa / 1) CHCl₃, 0 deg C, 1 hr, 2) CCl₄, reflux

8: 80 percent / (TMS)2NLi / tetrahydrofuran / 0.05 h / -78 °C

9: (i-C₃H₇)2NC₂H₅ / acetonitrile / 0 °C

With hydrogenchloride; aluminium trichloride; N-oxo-N-nitrosoamine; ammonium acetate; hydrogen; sodium acetate; magnesium oxide; dinitrogen tetraoxide; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)80262-8

Reference yield:

diethyl 2-ethyl-3-oxoglutarate (16631-50-8) → (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (84572-82-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) NaBH₃CN, AcONH₄, 2) 6N HCl / 1) ethanol, 2) heating

2: MgO / H₂O

3: 1) H₂ / 1) Pd-C, 2) TsOH

4: 73 percent / CH₂Cl₂ / 10 h / Ambient temperature

5: AlCl₃ / various solvent(s) / 3 h / Ambient temperature

6: DCC

7: 1) N₂O₂, CH₃COONa / 1) CHCl₃, 0 deg C, 1 hr, 2) CCl₄, reflux

8: 83 percent / (TMS)2NLi / tetrahydrofuran / 0.05 h / -78 °C

9: (i-C₃H₇)2NC₂H₅ / acetonitrile / 0 °C

With hydrogenchloride; aluminium trichloride; N-oxo-N-nitrosoamine; ammonium acetate; hydrogen; sodium acetate; magnesium oxide; sodium cyanoborohydride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)80262-8

Reference yield:

(2S,3S)-3-Amino-2-ethyl-pentanedioic acid (92445-54-0,92445-55-1) → (5R,6R)-3-(Diphenoxy-phosphoryloxy)-6-ethyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (84572-82-7)

Guidance literature:

Multi-step reaction with 8 steps

1: MgO / H₂O

2: 1) H₂ / 1) Pd-C, 2) TsOH

3: 73 percent / CH₂Cl₂ / 10 h / Ambient temperature

4: AlCl₃ / various solvent(s) / 3 h / Ambient temperature

5: DCC

6: 1) N₂O₂, CH₃COONa / 1) CHCl₃, 0 deg C, 1 hr, 2) CCl₄, reflux

7: 83 percent / (TMS)2NLi / tetrahydrofuran / 0.05 h / -78 °C

8: (i-C₃H₇)2NC₂H₅ / acetonitrile / 0 °C

With aluminium trichloride; N-oxo-N-nitrosoamine; hydrogen; sodium acetate; magnesium oxide; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; lithium hexamethyldisilazane; palladium on activated charcoal; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/S0040-4039(01)80262-8

upstream raw materials:

diethyl 2-ethyl-3-oxoglutarate

(2S,3R)-3-Amino-2-ethyl-pentanedioic acid

(2S,3R)-3-Amino-2-ethyl-pentanedioic acid 5-benzyl ester

(2S,3R)-3-Benzyloxycarbonylamino-2-ethyl-pentanedioic acid

Downstream raw materials:

PS-5

p-Nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate