2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester

Base Information

• Chemical Name: 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester
• CAS No.: 86269-30-9
• Molecular Formula: C₃₄H₂₉N₃O₁₀S
• Molecular Weight: 671.684
• Mol file: 86269-30-9.mol

Synonyms:

Chemical Property of 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester

There total 2 articles about 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl 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:

(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (59034-26-3) → 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester (86269-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh₂(OCOCH₃)4 / benzene; CH₂Cl₂

2: N(C₂H₅)3

With dirhodium tetraacetate; triethylamine; In dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)81695-0

Reference yield:

4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1) → 2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester (86269-30-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh₂(OCOCH₃)4 / benzene; CH₂Cl₂

2: N(C₂H₅)3

With dirhodium tetraacetate; triethylamine; In dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)81695-0

Reference yield:

2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(Z)-2-hydroxy-1-(4-nitro-benzyloxycarbonyl)-propenylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester (86269-30-9) → (5R,6R)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2,3-dicarboxylic acid bis-(4-nitro-benzyl) ester (87096-00-2)

Guidance literature:

Multi-step reaction with 8 steps

1: p-TsOH

2: KMnO₄

6: 80 percent / HClO₄

7: ozone, CF₃COOH / CH₂Cl₂

8: benzene / 80 °C

With potassium permanganate; perchloric acid; toluene-4-sulfonic acid; ozone; trifluoroacetic acid; In dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)81695-0

upstream raw materials:

(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

4-nitrobenzyl 2-diazo-3-oxo-butanoate

Downstream raw materials:

2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid benzyl ester

[(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-(2-methyl-[1,3]dioxolan-2-yl)-acetic acid 4-nitro-benzyl ester

(5R,6R)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2,3-dicarboxylic acid bis-(4-nitro-benzyl) ester

(6R,7R)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,4-dicarboxylic acid bis-(4-nitro-benzyl) ester