(3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one

Base Information

• Chemical Name: (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one
• CAS No.: 86489-42-1
• Molecular Formula: C₁₈H₂₄N₂O₈
• Molecular Weight: 396.397
• Mol file: 86489-42-1.mol

Synonyms:(3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one

Chemical Property of (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one

There total 4 articles about (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-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:

methyl 3-methyl-2-[(3R,4R)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-2-oxo-4-allylazetidin-1-yl]but-2-enoate (86541-15-3) → (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (86489-42-1)

Guidance literature:

With pyridine; hydrogenchloride; dimethylsulfide; p-toluenesulfonic acid monohydrate; trimethyl orthoformate; In methanol; water; ethyl acetate;

Reference yield:

methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (86489-13-6) → (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (86489-42-1)

Guidance literature:

Multi-step reaction with 3 steps

1: n-Bu₃SnH / AIBN / benzene / Heating

2: 1.) n-BuLi / 2.) ozonolysis

3: 1.) TsOH / 2.) methanolysis

With n-butyllithium; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; 2,2'-azobis(isobutyronitrile); In benzene;

DOI:10.1016/S0040-4039(00)61885-3

Reference yield:

methyl 3-methyl-2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]but-2-enoate (86541-14-2) → (3R,4R)-4-(2,2-dimethoxyethyl)-3-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-azetidin-2-one (86489-42-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 2.) ozonolysis

2: 1.) TsOH / 2.) methanolysis

With n-butyllithium; toluene-4-sulfonic acid;

DOI:10.1016/S0040-4039(00)61885-3

upstream raw materials:

[(3R,4R)-3-[1-Methyl-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-2-oxo-4-(2-oxo-ethyl)-azetidin-1-yl]-oxo-acetic acid methyl ester

trimethyl orthoformate

methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

methyl 3-methyl-2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-2-oxo-4-allylazetidin-1-yl]but-2-enoate

Downstream raw materials:

4-nitrobenzyl 2-diazo-4-[(2R,3R)-3-{1-methyl-1-(4-nitrobenzyloxycarbonyloxy)-ethyl}-4-oxoazetidin-2-yl]-3-oxobutanoate

4-nitrobenzyl (5R,6R)-3-[(Z)-2-acetamidovinyl-thio]-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo [3.2.0] hept-2-ene-2-carboxylate

4-nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

4-nitrobenzyl (5R,6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-[2-(4-nitrobenzyloxycarbonylamino)ethylthio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate