((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid

Base Information

• Chemical Name: ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid
• CAS No.: 218786-55-1
• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.408

Synonyms:((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid

Chemical Property of ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid

Chemical Property:

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Technology Process of ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid

There total 9 articles about ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.0^1,6]dodec-8-yl)-acetic acid 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:

(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione (33879-04-8,51065-67-9) → ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.01,6]dodec-8-yl)-acetic acid (218786-55-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CeCl₃ / 1.) THF, r.t., overnight, 2.) THF, -78 deg C

2: H₂, HClO₄ / 10percent Pd/C / ethanol

3: NH₂NH₂, TEA / ethanol

4: I₂, TEA / tetrahydrofuran

5: NH₂NH₂, O₂, AcOH / ethanol / Heating

6: tris(trimethylsilyl)silane, AIBN / toluene / 90 °C

7: DBU / diethyl ether / 0 - 20 °C

With perchloric acid; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; TEA; hydrogen; iodine; oxygen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; toluene;

DOI:10.1055/s-1998-1902

Reference yield:

phenyllithium (591-51-5) → ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.01,6]dodec-8-yl)-acetic acid (218786-55-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) CeCl₃ / 1.) THF, r.t., overnight, 2.) THF, -78 deg C

2: H₂, HClO₄ / 10percent Pd/C / ethanol

3: NH₂NH₂, TEA / ethanol

4: I₂, TEA / tetrahydrofuran

5: NH₂NH₂, O₂, AcOH / ethanol / Heating

6: tris(trimethylsilyl)silane, AIBN / toluene / 90 °C

7: DBU / diethyl ether / 0 - 20 °C

With perchloric acid; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane; TEA; hydrogen; iodine; oxygen; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; hydrazine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; toluene;

DOI:10.1055/s-1998-1902

Reference yield:

3-((1R,3aS,5S,7aR)-3a-Hydroxy-7a-methyl-5-phenyl-octahydro-inden-1-yl)-dihydro-furan-2,5-dione → ((1S,3S,6R,7R)-6-Methyl-9-oxo-3-phenyl-10-oxa-tricyclo[5.3.2.01,6]dodec-8-yl)-acetic acid (218786-55-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In diethyl ether; at 0 - 20 ℃; Yield given;

DOI:10.1055/s-1998-1902

upstream raw materials:

(+)-(3aS,7aS)-2,3,3a,4,7,7a-hexahydro-3a-hydroxy-7a-methyl-1H-indene-1,5(6H)-dione

phenyllithium

(1R,3aS,5S,7aS)-1-Iodo-7a-methyl-5-phenyl-octahydro-inden-3a-ol

(3aS,5S,7aS)-3a-Hydroxy-7a-methyl-5-phenyl-octahydro-inden-1-one

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