2-{(2R,3S)-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,3S)-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.: 100163-33-5
• Molecular Formula: C₃₄H₂₉N₃O₁₀S
• Molecular Weight: 671.684
• Mol file: 100163-33-5.mol

Synonyms:2-{(2R,3S)-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 of 2-{(2R,3S)-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,3S)-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 3 articles about 2-{(2R,3S)-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:

(Z)-2-[(2R,3S)-1-((R)-1-Benzyloxycarbonyl-2-methyl-allyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-3-hydroxy-but-2-enoic acid 4-nitro-benzyl ester (86255-97-2,86288-03-1,100163-31-3) → 2-{(2R,3S)-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 (100163-33-5)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h; Yield given;

DOI:10.1021/jo00355a011

Reference yield:

4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1) → 2-{(2R,3S)-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 (100163-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh₂(OAc)4 / benzene; CH₂Cl₂ / 16 h / Heating

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dirhodium tetraacetate; triethylamine; In dichloromethane; benzene;

DOI:10.1021/jo00355a011

Reference yield:

(2S,5R,6S)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (66363-43-7) → 2-{(2R,3S)-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 (100163-33-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Rh₂(OAc)4 / benzene; CH₂Cl₂ / 16 h / Heating

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

With dirhodium tetraacetate; triethylamine; In dichloromethane; benzene;

DOI:10.1021/jo00355a011

upstream raw materials:

(Z)-2-[(2R,3S)-1-((R)-1-Benzyloxycarbonyl-2-methyl-allyl)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-3-hydroxy-but-2-enoic acid 4-nitro-benzyl ester

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

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

Refernces