(5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Base Information

• Chemical Name: (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate
• CAS No.: 133380-98-0
• Molecular Formula: C₃₆H₃₀N₃O₁₁PS
• Molecular Weight: 743.687
• Mol file: 133380-98-0.mol

Synonyms:(5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property of (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

There total 10 articles about (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate 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: 64.0%

diphenylthiophosphinoyl chloride (1015-37-8) + (5RS,6RS,8RS)-p-nitrobenzyl 3,7-dioxo-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate (76335-78-9,77448-03-4,92693-52-2,117407-10-0,133443-89-7) → (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (133380-98-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In acetonitrile; at 0 ℃; for 0.5h;

Reference yield:

(6RS,9RS)-7-chloro-7-(1-hydroxyethyl)-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane (106673-95-4,106758-30-9,133443-86-4,142924-03-6) → (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (133380-98-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 49 percent / tributyltin hydride, azobisisobutyronitrile / acetone / 6 h / Heating

2: 1) lithium diisopropylamide / 1) THF, -70 deg C, 10 min, 2) up to r.t., 1 h

3: 5 M sulphuric acid / 24 h / 50 °C

4: Jones'reagent / acetone / 0.5 h / 0 °C

5: tetrahydrofuran / 7 h

6: tetrahydrofuran / 18 h

7: 100 percent / toluene-p-sulphonyl azide, triethylamine / acetonitrile / 1.5 h

8: 100 percent / rhodium acetate / benzene / 1 h / Heating

9: 64 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C

With rhodium(II) acetate; 4-toluenesulfonyl azide; 2,2'-azobis(isobutyronitrile); Jones'reagent; sulfuric acid; tri-n-butyl-tin hydride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; acetone; acetonitrile; benzene;

Reference yield:

7-acetyl-7-chloro-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane (106673-91-0,142836-84-8) → (5RS,6RS,8RS)-p-nitrobenzyl 3-diphenylthiophosphinoyl-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (133380-98-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / L-Selectride / tetrahydrofuran / 1 h / -70 °C

2: 49 percent / tributyltin hydride, azobisisobutyronitrile / acetone / 6 h / Heating

3: 1) lithium diisopropylamide / 1) THF, -70 deg C, 10 min, 2) up to r.t., 1 h

4: 5 M sulphuric acid / 24 h / 50 °C

5: Jones'reagent / acetone / 0.5 h / 0 °C

6: tetrahydrofuran / 7 h

7: tetrahydrofuran / 18 h

8: 100 percent / toluene-p-sulphonyl azide, triethylamine / acetonitrile / 1.5 h

9: 100 percent / rhodium acetate / benzene / 1 h / Heating

10: 64 percent / diisopropylethylamine / acetonitrile / 0.5 h / 0 °C

With rhodium(II) acetate; 4-toluenesulfonyl azide; 2,2'-azobis(isobutyronitrile); Jones'reagent; sulfuric acid; tri-n-butyl-tin hydride; L-Selectride; triethylamine; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; acetone; acetonitrile; benzene;

upstream raw materials:

diphenylthiophosphinoyl chloride

(5RS,6RS,8RS)-p-nitrobenzyl 3,7-dioxo-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-1-azabicyclo<3.2.0>heptane-2-carboxylate

(6RS,9RS)-7-chloro-7-(1-hydroxyethyl)-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane

7-acetyl-7-chloro-8-oxo-3-oxa-1-azabicyclo<4.2.0>octane-2-spirocyclohexane

Downstream raw materials:

(5RS,6RS,8RS)-p-nitrobenzyl 3-<2-(p-nitrobenzyloxycarbonylamino)ethylthio>-6-(1-p-nitrobenzyloxycarbonyloxyethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate