{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester
• CAS No.: 83860-44-0
• Molecular Formula: C₂₃H₃₀N₂O₇S₃Si
• Molecular Weight: 570.784
• Mol file: 83860-44-0.mol

Synonyms:

Chemical Property of {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester

There total 1 articles about {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-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:

carbon disulfide (75-15-0,12122-00-8) + phosgene (75-44-5) + (3S,4R)-3-<(R)-1-tert-Butyldimethylsilyloxyethyl>-4-methylthio-2-oxoazetidine (82864-29-7) → {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester (83860-44-0)

Guidance literature:

Multistep reaction;

DOI:10.1039/c39820000713

Reference yield:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester (83860-44-0) → {(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester (83807-48-1)

Guidance literature:

With chlorine; In dichloromethane; at 0 ℃;

DOI:10.1039/c39820000713

Reference yield:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester (83860-44-0) → (5R,6S)-3-Cyanomethylsulfanyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (81878-57-1)

Guidance literature:

Multi-step reaction with 5 steps

1: Cl₂ or SO₂Cl / CH₂Cl₂ / 0 °C

2: MeNH₂ / methanol; CH₂Cl₂

3: Et₃N / CH₂Cl₂ / Ambient temperature

4: hydroquinone / xylene / 5 h / Heating

5: Bu₄NF

With tetrabutyl ammonium fluoride; chlorine; triethylamine; hydroquinone; methylamine; In methanol; dichloromethane; xylene;

DOI:10.1039/c39820000713

upstream raw materials:

carbon disulfide

phosgene

(3S,4R)-3-<(R)-1-tert-Butyldimethylsilyloxyethyl>-4-methylthio-2-oxoazetidine

Downstream raw materials:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-chloro-4-oxo-azetidin-1-yl}-(4-oxo-[1,3]dithietan-2-ylidene)-acetic acid 4-nitro-benzyl ester

(5R,6S)-3-Cyanomethylsulfanyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

(5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester