(3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester
• CAS No.: 211623-29-9
• Molecular Formula: C₂₃H₂₂N₂O₅S
• Molecular Weight: 438.504

Synonyms:(3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester

Chemical Property of (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester

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Technology Process of (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester

There total 4 articles about (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-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:

benzhydryl 6-(allyloxycarbonylamino)penicillinate (121464-10-6) → (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.03,11]dodecane-12-carboxylic acid benzhydryl ester (211623-29-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / MCPBA

2: 100 percent / toluene / Heating

3: 1.) AgOAc, 2.) Pd(PPh₃)4, Bu₃SnH, 3.) NaHCO₃

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; silver(I) acetate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In toluene;

DOI:10.1021/ja980195z

Reference yield:

(2S,4S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-4,7-dioxo-4λ4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (211623-24-4) → (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.03,11]dodecane-12-carboxylic acid benzhydryl ester (211623-29-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / toluene / Heating

2: 1.) AgOAc, 2.) Pd(PPh₃)4, Bu₃SnH, 3.) NaHCO₃

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; silver(I) acetate; sodium hydrogencarbonate; In toluene;

DOI:10.1021/ja980195z

Reference yield:

6-aminopenicillanic acid diphenylmethyl ester (47547-28-4,78184-79-9) → (3R,9R,11R,12S)-9-Methyl-2,6-dioxo-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.03,11]dodecane-12-carboxylic acid benzhydryl ester (211623-29-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / pyridine

2: 96 percent / MCPBA

3: 100 percent / toluene / Heating

4: 1.) AgOAc, 2.) Pd(PPh₃)4, Bu₃SnH, 3.) NaHCO₃

With pyridine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; silver(I) acetate; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In toluene;

DOI:10.1021/ja980195z

upstream raw materials:

chloroacetic acid

(R)-benzhydryl 2-((2R,3R)-3-(allyloxycarbonyl)amino-2-(benzo[d]thiazol-2-yldisulfanyl)-4-oxoazetidin-1-yl)-3-methylbut-3-enoate

benzhydryl 6-(allyloxycarbonylamino)penicillinate

(2S,4S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-4,7-dioxo-4λ⁴-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Downstream raw materials:

(3R,9R,11R,12S)-9-Methyl-2,6-dioxo-4-phenylacetyl-7-oxa-10-thia-1,4-diaza-tricyclo[7.2.1.0^3,11]dodecane-12-carboxylic acid benzhydryl ester

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