Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester

Base Information

• Chemical Name: Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester
• CAS No.: 72778-03-1
• Molecular Formula: C₁₅H₁₆N₂O₇
• Molecular Weight: 336.301
• Mol file: 72778-03-1.mol

Synonyms:Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester

Chemical Property of Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester

There total 13 articles about Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl 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:

trans-4-methoxycarbonyl-3-(2',2'-dimethoxyethyl)-5-methylisoxazoline (72447-82-6,72843-52-8,78088-41-2,78778-11-7) → Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester (72778-03-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 5.08 g / hydrogen / PtO₂ / acetic acid / 72 h / Ambient temperature

2: Na, H₂O, MeOH / 4.5 h / Heating

3: 908 mg / N,N'-dicyclohexylcarbodiimide / dioxane; H₂O / 12 h / Heating

4: 85 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

5: AcOH, H₂O / 5 h / 60 °C

With methanol; dmap; water; hydrogen; sodium; acetic acid; dicyclohexyl-carbodiimide; platinum(IV) oxide; In 1,4-dioxane; dichloromethane; water; acetic acid;

DOI:10.1021/ja00526a048

Reference yield:

trans-3-(2',2'-dimethoxyethyl)-5-methylisoxazoline-4-carboxylic acid (73844-78-7,78778-12-8) → Carbonic acid 4-nitro-benzyl ester 1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester (72778-03-1)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen / PtO₂ / acetic acid / 48 h / Ambient temperature

2: 908 mg / N,N'-dicyclohexylcarbodiimide / dioxane; H₂O / 12 h / Heating

3: 85 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

4: AcOH, H₂O / 5 h / 60 °C

With dmap; water; hydrogen; acetic acid; dicyclohexyl-carbodiimide; platinum(IV) oxide; In 1,4-dioxane; dichloromethane; water; acetic acid;

DOI:10.1021/ja00526a048

Reference yield:

trans-4-methoxycarbonyl-3-(2',2'-dimethoxyethyl)-5-methylisoxazoline (72447-82-6,72843-52-8,78088-41-2,78778-11-7) → Carbonic acid 4-nitro-benzyl ester (S)-1-[(3R,4S)-2-oxo-4-(2-oxo-ethyl)-azetidin-3-yl]-ethyl ester (64066-71-3,67314-42-5,71869-79-9,72778-03-1,77447-99-5,80559-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 5.08 g / hydrogen / PtO₂ / acetic acid / 72 h / Ambient temperature

2: 10.1 percent / methylmagnesium iodide / diethyl ether; tetrahydrofuran / 18 h / Ambient temperature

3: 83 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 0 °C

4: AcOH, H₂O / 4.5 h / 60 °C

With dmap; methyl magnesium iodide; water; hydrogen; acetic acid; platinum(IV) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid;

DOI:10.1021/ja00526a048

upstream raw materials:

Carbonic acid 1-[(2S,3R)-2-(2-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester 4-nitro-benzyl ester

trans-4-(2',2'-dimethoxyethyl)-3-(1'-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

(+/-)-4β-(2',2'-dimethoxyethyl)-3α-((1'R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine

Downstream raw materials:

Carbonic acid 1-((2S,3R)-2-{2,2-bis-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-ethyl}-4-oxo-azetidin-3-yl)-ethyl ester 4-nitro-benzyl ester

(+/-)-4β-(2'-hydroxyethyl)-3α-((1'R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

Carbonic acid (R)-1-[(2S,3R)-2-(2-hydroxy-ethyl)-4-oxo-azetidin-3-yl]-ethyl ester 4-nitro-benzyl ester

(2S,5S,6S)-3-[2-(4-Nitro-benzyloxycarbonylamino)-ethylsulfanyl]-6-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-3-ene-2-carboxylic acid 4-nitro-benzyl ester