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

Base Information

• Chemical Name: methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate
• CAS No.: 80559-15-5
• Molecular Formula: C₂₀H₂₄N₂O₈S
• Molecular Weight: 452.485
• Mol file: 80559-15-5.mol

Synonyms:methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate

Chemical Property of methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate

There total 2 articles about methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate 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:

(3S,4R)-3-(1-hidroxyethyl)-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-methylthio-2-azetidinone (74614-77-0,76899-00-8,76899-01-9) + 4-nitrobenzyl chloroformate (4457-32-3) → methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate (80559-15-5)

Guidance literature:

With dmap; In dichloromethane; ethyl acetate;

Reference yield:

(3S,4R)-3-(1-hidroxyethyl)-1-(1-methoxycarbonyl-2-methyl-1-propenyl)-4-methylthio-2-azetidinone (74614-77-0,76899-00-8,76899-01-9) + 4-nitrobenzyl chloroformate (4457-32-3) → methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1S)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-but-2-enoate (76855-55-5) + methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate (80559-15-5)

Guidance literature:

With dmap; In dichloromethane; at 0 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)87743-6

Reference yield: 84.0%

methyl 3-methyl-2-[(3S,4R)-4-methylthio-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]but-2-enoate (80559-15-5) → methyl 2-[(3S)-4-chloro-3-{(1R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl}-2-oxoazetidin-1-yl]-3-methylbut-2-enoate (80527-82-8,80559-16-6,80559-17-7,80559-18-8,102919-74-4)

Guidance literature:

With chlorine; In tetrachloromethane; dichloromethane; at -78 - 0 ℃; cis/trans ratio: 45:55;

DOI:10.1016/S0040-4039(00)87743-6

upstream raw materials:

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

4-nitrobenzyl chloroformate

Downstream raw materials:

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

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

4-{(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-2-yl}-3-oxo-butyric acid 4-nitro-benzyl ester