[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester
• CAS No.: 78902-71-3
• Molecular Formula: C₄₃H₅₁N₂O₇PS₃Si
• Molecular Weight: 863.144

Synonyms:[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Chemical Property of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

Chemical Property:

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Safty Information:

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Technology Process of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

There total 3 articles about [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-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:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (78902-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: methanol / 0.67 h / -10 °C

2: 100 percent / benzene / 10 h / Heating

3: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

With 2,6-dimethylpyridine; thionyl chloride; In methanol; benzene;

DOI:10.1248/cpb.29.3158

Reference yield:

Trithiocarbonic acid (2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-ethoxy-ethyl ester (78902-69-9,81076-31-5) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (78902-71-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / benzene / 10 h / Heating

2: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

With 2,6-dimethylpyridine; thionyl chloride; In benzene;

DOI:10.1248/cpb.29.3158

Reference yield:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester (78902-70-2,78963-61-8,81076-32-6) + triphenylphosphine (603-35-0) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (78902-71-3)

Guidance literature:

With 2,6-dimethylpyridine; thionyl chloride; Yield given. Multistep reaction; 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h;

DOI:10.1248/cpb.29.3158

upstream raw materials:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-ethoxy-ethylsulfanylthiocarbonylsulfanyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester

triphenylphosphine

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

Trithiocarbonic acid (2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl ester 2-ethoxy-ethyl ester

Downstream raw materials:

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

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

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