(2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

Base Information

• Chemical Name: (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene
• CAS No.: 195819-04-6
• Molecular Formula: C₁₉H₂₁NO₄
• Molecular Weight: 327.38

Synonyms:(2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

Chemical Property of (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

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Technology Process of (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

There total 3 articles about (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene 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: 89.0%

(2R,5S,6S,11S)-11-ethoxycarbonyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.01,5.06,11]dodec-8-ene (166765-37-3) → (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.01,5.06,11]dodec-8-ene (195819-04-6)

Guidance literature:

With sodium hydroxide; In water; acetonitrile; at 20 ℃; for 17h;

DOI:10.1016/S0040-4020(97)00740-0

Reference yield:

(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene (166765-36-2) → (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.01,5.06,11]dodec-8-ene (195819-04-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / toluene / 72 h / Heating

2: 89 percent / NaOH / H₂O; acetonitrile / 17 h / 20 °C

With sodium hydroxide; In water; toluene; acetonitrile; 1: Cycloaddition / 2: Hydrolysis;

DOI:10.1016/S0040-4020(97)00740-0

Reference yield:

(3R,7aS)-5-Oxo-3-phenyl-6-phenylselanyl-tetrahydro-pyrrolo[1,2-c]oxazole-6-carboxylic acid ethyl ester → (2R,5S,6S,11S)-11-carboxyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.01,5.06,11]dodec-8-ene (195819-04-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 84 percent / hydrogen peroxide / CH₂Cl₂ / 0.5 h / 30 °C

2: 72 percent / toluene / 72 h / Heating

3: 89 percent / NaOH / H₂O; acetonitrile / 17 h / 20 °C

With sodium hydroxide; dihydrogen peroxide; In dichloromethane; water; toluene; acetonitrile; 1: Oxidation / 2: Cycloaddition / 3: Hydrolysis;

DOI:10.1016/S0040-4020(97)00740-0

upstream raw materials:

(2R,5S,6S,11S)-11-ethoxycarbonyl-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

(2R,5S)-7-ethoxycarbonyl-8-oxo-2-phenyl-1-aza-3-oxa-bicyclo[3.3.0]oct-6-ene

Downstream raw materials:

(2R,5S,6S,11R)-8,9-dimethyl-12-oxo-2-phenyl-1-aza-3-oxa-tricyclo[7.3.0^1,5.0^6,11]dodec-8-ene

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