p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate

Base Information

• Chemical Name: p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate
• CAS No.: 92882-53-6
• Molecular Formula: C₅₀H₅₅N₄O₁₁PSi
• Molecular Weight: 947.066
• Mol file: 92882-53-6.mol

Synonyms:p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate

Chemical Property of p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate

There total 6 articles about p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate 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:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate (92882-53-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / boron trifluoride etherate / CH₂Cl₂ / 15 h / Ambient temperature

2: 650 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / Ambient temperature

3: 77 percent / dimethylformamide / 15 h / Ambient temperature

4: 1.) H₂; 2.) N,N-diisopropylethylamine / 1.) PtO₂ / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH₂Cl₂, roomtemp.

5: 66 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

6: 86 percent / triethylamine / benzene / 6 h / Heating

7: 1.) thionyl chloride, 2,6-lutidine / 1.) THF, -30 deg C, 1 h; 2.) dioxane, roomtemp.

With 2,6-dimethylpyridine; thionyl chloride; boron trifluoride diethyl etherate; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; platinum(IV) oxide; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.59.1363

Reference yield:

(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone (80433-47-2) → p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate (92882-53-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 650 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / Ambient temperature

2: 77 percent / dimethylformamide / 15 h / Ambient temperature

3: 1.) H₂; 2.) N,N-diisopropylethylamine / 1.) PtO₂ / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH₂Cl₂, roomtemp.

4: 66 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

5: 86 percent / triethylamine / benzene / 6 h / Heating

6: 1.) thionyl chloride, 2,6-lutidine / 1.) THF, -30 deg C, 1 h; 2.) dioxane, roomtemp.

With 2,6-dimethylpyridine; thionyl chloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; platinum(IV) oxide; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1246/bcsj.59.1363

Reference yield:

(3S,4R)-4-(3-cyano-2-hydroxypropyl)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-2-azetidinone (92838-69-2,96613-74-0,96613-75-1) → p-nitrobenzyl 2-<(3S,4R)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-oxo-1-azetidinyl>-2-triphenylphosphoranylideneacetate (92882-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) H₂; 2.) N,N-diisopropylethylamine / 1.) PtO₂ / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH₂Cl₂, roomtemp.

2: 66 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 86 percent / triethylamine / benzene / 6 h / Heating

4: 1.) thionyl chloride, 2,6-lutidine / 1.) THF, -30 deg C, 1 h; 2.) dioxane, roomtemp.

With 2,6-dimethylpyridine; thionyl chloride; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; platinum(IV) oxide; In dichloromethane; benzene;

DOI:10.1246/bcsj.59.1363

upstream raw materials:

triphenylphosphine

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3S,4R)-3-[(1R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-(prop-2-enyl)-2-azetidinone

(3S,4R)-4-(3-cyano-2-hydroxypropyl)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-2-azetidinone