Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

Base Information

Chemical Name:Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester
CAS No.:132042-00-3
Molecular Formula:C₃₃H₅₂O₄Si
Molecular Weight:540.859
Hs Code.:

Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

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Chemical Property of Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

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Technology Process of Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

There total 11 articles about Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl 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:

: 132042-02-5
2,2-Dimethoxy-1-(2-furanyl)-6-methyl-6-hepten-1-ol

: 132042-00-3
Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

Guidance literature:: Multi-step reaction with 11 steps

1: 1) O₂, Rose Bengal, 2) DMS / 1) CH₂Cl₂, CH₃OH, irradiation, -78 deg C, 2) -78 to 22 deg C

2: 1) AcCl, pyridine, 2) DBU / 1) CH₂Cl₂, 0 deg C, 2) 22 deg C

3: 86 percent / L-Selectride / tetrahydrofuran / -78 °C

4: 1) LDA, 2) DMPU / 1) THF, -78 deg C, 40 min, 2) -78 to 22 deg C

5: 1) LDA, 2) DMPU / 1) THF, -78 deg C

6: 73 percent / aq.HClO₄ / methanol / Heating

7: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

8: 90 percent / Et₃N, DMAP / CH₂Cl₂; dimethylformamide / 0 - 22 °C

9: 77 percent / SOCl₂, pyridine / CH₂Cl₂ / -10 - 22 °C

10: Na naphthalenide / tetrahydrofuran

11: Et₃N, DMAP / CH₂Cl₂

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; thionyl chloride; perchloric acid; cerium(III) chloride; 2,3-dimercapto-succinic acid; Na naphthalenide; oxygen; L-Selectride; rose bengal; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; acetyl chloride; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)97167-3

Reference yield:

: 132042-06-9
(1R,6R,8R)-2,2-Dimethoxy-6-methyl-12-oxa-tricyclo[6.3.1.0^1,6]dodecan-11-one

: 132042-00-3
Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 1) LDA, 2) DMPU / 1) THF, -78 deg C, 40 min, 2) -78 to 22 deg C

2: 1) LDA, 2) DMPU / 1) THF, -78 deg C

3: 73 percent / aq.HClO₄ / methanol / Heating

4: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

5: 90 percent / Et₃N, DMAP / CH₂Cl₂; dimethylformamide / 0 - 22 °C

6: 77 percent / SOCl₂, pyridine / CH₂Cl₂ / -10 - 22 °C

7: Na naphthalenide / tetrahydrofuran

8: Et₃N, DMAP / CH₂Cl₂

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; thionyl chloride; perchloric acid; cerium(III) chloride; Na naphthalenide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)97167-3

Reference yield:

: 132042-05-8
(+/-)-(1S*,6S*,8R*)-2,2-Dimethoxy-6-methyl-12-oxatricyclo<6.3.1.0^1,6>dodec-9-en-11-one

: 132042-00-3
Benzoic acid (4aR,6S,8R)-8-[3-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentyl]-1,4a,8-trimethyl-9-oxo-3,4,4a,5,6,7,8,9-octahydro-2H-benzocyclohepten-6-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / L-Selectride / tetrahydrofuran / -78 °C

2: 1) LDA, 2) DMPU / 1) THF, -78 deg C, 40 min, 2) -78 to 22 deg C

3: 1) LDA, 2) DMPU / 1) THF, -78 deg C

4: 73 percent / aq.HClO₄ / methanol / Heating

5: 79 percent / CeCl₃ / tetrahydrofuran / -78 °C

6: 90 percent / Et₃N, DMAP / CH₂Cl₂; dimethylformamide / 0 - 22 °C

7: 77 percent / SOCl₂, pyridine / CH₂Cl₂ / -10 - 22 °C

8: Na naphthalenide / tetrahydrofuran

9: Et₃N, DMAP / CH₂Cl₂

With pyridine; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; thionyl chloride; perchloric acid; cerium(III) chloride; Na naphthalenide; L-Selectride; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(00)97167-3