(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 benzyl 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 benzyl ester
• CAS No.: 211623-37-9
• Molecular Formula: C₁₇H₁₈N₂O₅S
• Molecular Weight: 362.406

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 benzyl 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 benzyl 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 benzyl 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 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:

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (3956-31-8,49626-54-2,64519-71-7) → (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 benzyl ester (211623-37-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine

2: 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

Reference yield:

(2S,5R,6R)-6-Allyloxycarbonylamino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester (211623-32-4) → (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 benzyl ester (211623-37-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 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 benzyl ester (211623-33-5) → (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 benzyl ester (211623-37-9)

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

upstream raw materials:

chloroacetic acid

(R)-2-[(2R,3R)-3-Allyloxycarbonylamino-2-(benzothiazol-2-yldisulfanyl)-4-oxo-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

benzyl (2S,5R,6R)-6-amino-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

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

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