(4R,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

Base Information

• Chemical Name: (4R,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
• CAS No.: 90211-63-5
• Molecular Formula: C₃₂H₂₈N₄O₅S₂
• Molecular Weight: 612.73

Synonyms:(4R,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

Chemical Property of (4R,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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Technology Process of (4R,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

There total 10 articles about (4R,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 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: 81.0%

(3R,4R)-4-{(1R)-3-(2-methyl-1,3,4-thiadiazole-5-yl)thio-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (90211-62-4) → (4R,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 (90211-63-5)

Guidance literature:

With hydroquinone; In toluene; for 11h; Heating;

DOI:10.3987/COM-90-5345

Reference yield:

(3R,4R)-4-{(1R)-1-carboxyethoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (90211-54-4) → (4R,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 (90211-63-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 4-methylmorpholine / CH₂Cl₂ / 0.5 h / -10 °C

3: rhodium(II) acetate dimer / ethyl acetate / 0.67 h / 60 °C

4: 81 percent / hydroquinone / toluene / 11 h / Heating

With 4-methyl-morpholine; dirhodium tetraacetate; hydroquinone; In dichloromethane; ethyl acetate; toluene;

DOI:10.3987/COM-90-5345

Reference yield:

(3R,4R)-4-{(1R)-3-diazo-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one (90211-56-6) → (4R,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 (90211-63-5)

Guidance literature:

Multi-step reaction with 2 steps

1: rhodium(II) acetate dimer / ethyl acetate / 0.67 h / 60 °C

2: 81 percent / hydroquinone / toluene / 11 h / Heating

With dirhodium tetraacetate; hydroquinone; In ethyl acetate; toluene;

DOI:10.3987/COM-90-5345

upstream raw materials:

(3R,4R)-4-{(1R)-3-(2-methyl-1,3,4-thiadiazole-5-yl)thio-2-oxo-1-methylpropoxy}-3-benzamido-1-(1-diphenylmethoxycarbonyl-1-triphenylphosphoranylidenemethyl)azetidin-2-one

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

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

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

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