(+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

Base Information

• Chemical Name: (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone
• CAS No.: 65794-48-1
• Molecular Formula: C₃₅H₃₈N₆O₁₄S₂
• Molecular Weight: 830.851
• Mol file: 65794-48-1.mol

Synonyms:

Chemical Property of (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

There total 11 articles about (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone 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) → (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (65750-52-9,65794-48-1,72843-55-1,72843-57-3,78342-10-6,79057-47-9)

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: CF₃CO₂H / 16 h / Ambient temperature

With methanol; dmap; water; hydrogen; sodium; dicyclohexyl-carbodiimide; trifluoroacetic acid; 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) → (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (65750-52-9,65794-48-1,72843-55-1,72843-57-3,78342-10-6,79057-47-9)

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: CF₃CO₂H / 16 h / Ambient temperature

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

DOI:10.1021/ja00526a048

Reference yield:

methyl 3-amino-5-hydroxy-1,1-dimethoxyhexane-4-carboxylate (72447-84-8,72843-84-6,72843-85-7,73890-28-5,74111-43-6,78549-44-7,78549-45-8) → (+/-)-4β-<2',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (65750-52-9,65794-48-1,72843-55-1,72843-57-3,78342-10-6,79057-47-9)

Guidance literature:

Multi-step reaction with 4 steps

1: Na, H₂O, MeOH / 4.5 h / Heating

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

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

4: CF₃CO₂H / 16 h / Ambient temperature

With methanol; dmap; water; sodium; dicyclohexyl-carbodiimide; trifluoroacetic acid; In 1,4-dioxane; dichloromethane; water;

DOI:10.1021/ja00526a048

upstream raw materials:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

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

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

4-nitrobenzyl chloroformate

Downstream raw materials:

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

2-Chloro-2-{(2S,3S)-2-{(E)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

2-Hydroxy-2-{(2S,3S)-2-{(E)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester

2-Hydroxy-2-{(2S,3S)-2-{(Z)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-vinyl}-3-[1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-malonic acid bis-(4-nitro-benzyl) ester