[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Base Information

• Chemical Name: [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester
• CAS No.: 104634-56-2
• Molecular Formula: C₃₈H₄₈NO₆PSi
• Molecular Weight: 673.861

Synonyms:[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Chemical Property of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

Chemical Property:

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Technology Process of [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

There total 9 articles about [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl 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:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-methoxymethoxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (202993-81-5) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (104634-56-2)

Guidance literature:

With trimethylsilyl bromide; In dichloromethane; at -35 - -30 ℃; for 0.25h; Yield given;

DOI:10.1021/jo9716845

Reference yield:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (104634-56-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexane, -75 deg C, 30 min, 2.) THF, hexane, -78 deg C to 0 deg C, 3 h

2: 84 percent / toluene / 16 h / Heating

3: SO₂Cl, 2,6-lutidine / tetrahydrofuran / 1 h / -40 - -30 °C

4: 6.772 g / 2,6-lutidine, MS / dimethylformamide / 15 h / Ambient temperature

5: Me₃SiBr / CH₂Cl₂ / 0.25 h / -35 - -30 °C

With 2,6-dimethylpyridine; n-butyllithium; sulfuryl dichloride; trimethylsilyl bromide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo9716845

Reference yield:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (202993-86-0) → [(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-hydroxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid allyl ester (104634-56-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2.5h; Ambient temperature;

DOI:10.1021/jo9716845

upstream raw materials:

[(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-((R)-3-methoxymethoxy-1-methyl-2-oxo-propyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-3-(4-methoxy-benzyloxy)-1-methyl-2-oxo-propyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid allyl ester

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-3-methoxymethoxy-1-methyl-2-oxo-propyl)-azetidin-2-one

Downstream raw materials:

(4S,5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(1H-imidazol-2-ylamino)-methyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid

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