(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Base Information

• Chemical Name: (+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one
• CAS No.: 77447-98-4
• Molecular Formula: C₁₇H₂₂N₂O₈
• Molecular Weight: 382.37
• Mol file: 77447-98-4.mol

Synonyms:(+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Chemical Property of (+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

There total 18 articles about (+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one 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: 83.0%

trans-4-<(2',2'-dimethoxy)ethyl>-3-<(1'R)-hydroxyethyl>azetidin-2-one (72447-85-9,72496-42-5,72843-53-9,72843-54-0,73890-29-6,73890-30-9,74164-94-6,74164-95-7,78088-39-8,79299-24-4,79952-68-4,81076-43-9) + 4-nitrobenzyl chloroformate (4457-32-3) → (+/-)-4β-(2',2'-dimethoxyethyl)-3α-((1'R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (72789-82-3,72843-58-4,73890-31-0,73890-76-3,77447-98-4,78342-09-3,78822-11-4,79057-48-0,79299-23-3,79952-71-9)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/ja00526a048

Reference yield: 60.0%

cis-3-(1'R*-hydroxyethyl-4-(2',2'-dimethoxyethyl))-2-azetidinone (72447-85-9,72496-42-5,72843-53-9,72843-54-0,73890-29-6,73890-30-9,74164-94-6,74164-95-7,78088-39-8,79299-24-4,79952-68-4,81076-43-9) + 4-nitrobenzyl chloroformate (4457-32-3) → (+/-)-4β-(2,2-dimethoxyethyl)-3β-<(1S*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one (77447-98-4)

Guidance literature:

With dmap; In dichloromethane; at -5 - 0 ℃; for 1h;

DOI:10.1039/P19810002282

Reference yield:

3-Nitropropanal dimethyl acetal (72447-81-5) → trans-4-(2',2'-dimethoxyethyl)-3-(1'-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone (72789-82-3,72843-58-4,73890-31-0,73890-76-3,77447-98-4,78342-09-3,78822-11-4,79057-48-0,79299-23-3,79952-71-9)

Guidance literature:

Multi-step reaction with 6 steps

1: phenyl isocyanate, triethylamine / benzene / 1) room temperature, 24 h; 2) reflux, 5 h

2: 5 g / benzene

3: 5.08 g / hydrogen / PtO₂ / acetic acid / 72 h / Ambient temperature

4: Na, H₂O, MeOH / 4.5 h / Heating

5: 908 mg / N,N'-dicyclohexylcarbodiimide / dioxane; H₂O / 12 h / Heating

6: 85 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1 h / 0 °C

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

DOI:10.1021/ja00526a048

upstream raw materials:

methanol

methyl 3-methyl-2-[(3S,4R)-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxo-4-allylazetidin-1-yl]but-2-enoate

(3S,4R)-3-(1-hidroxyethyl)-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-methylthio-2-azetidinone

methyl 2-[(3S,4S)-4-chloro-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate

Downstream raw materials:

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

Carbonic acid (R)-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',2'-bis(2-p-nitrobenzyloxyaminoethylthio)ethyl>-3α-((1'-R*)-p-nitrobenzyloxycarbonyloxyethyl)-2-azetidinone

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