{(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Base Information

• Chemical Name: {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester
• CAS No.: 130793-04-3
• Molecular Formula: C₅₀H₄₃N₄O₆PS₂
• Molecular Weight: 891.02

Synonyms:{(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

Chemical Property of {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

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Technology Process of {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl ester

There total 11 articles about {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ⁵-phosphanylidene)-acetic acid benzhydryl 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: 96.0%

(3R,4R)-4-{(1S)-3-chloro-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (90244-30-7) + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (130793-04-3)

Guidance literature:

In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.3987/COM-90-5345

Reference yield: 63.0%

(3R,4R)-4-{(1S)-3-diazo-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (90244-29-4) + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (130793-04-3)

Guidance literature:

With dirhodium tetraacetate; In ethyl acetate; at 60 ℃; for 0.666667h;

DOI:10.3987/COM-90-5345

Reference yield:

[(2R,3R)-3-Benzoylamino-2-((S)-2-ethoxycarbonyloxy-1-methyl-2-oxo-ethoxy)-4-oxo-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (130675-27-3) → {(2R,3R)-3-Benzoylamino-2-[(S)-1-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propoxy]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid benzhydryl ester (130793-04-3)

Guidance literature:

Multi-step reaction with 3 steps

2: 100 percent / HCl / dioxane / 30 h / 5 °C

3: 96 percent / dimethylformamide / 1 h / Ambient temperature

With hydrogenchloride; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.3987/COM-90-5345

upstream raw materials:

(3R,4R)-4-{(1S)-3-chloro-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one

2-mercapto-5-methyl-1,3,4-thiadiazole

(3R,4R)-4-{(1S)-3-diazo-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one

(3R,4R)-4-{(1S)-1-carboxyethoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one

Downstream raw materials:

(4S,6R,7R)-7-Benzoylamino-4-methyl-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanylmethyl)-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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