methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

Base Information

Chemical Name:methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate
CAS No.:302840-48-8
Molecular Formula:C₁₉H₃₆O₃Si
Molecular Weight:340.579
Hs Code.:

Synonyms:methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

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Chemical Property of methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

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Technology Process of methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

There total 6 articles about methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate 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: 95.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 302840-46-6
methyl 2-[(1R,2R)-2-hydroxy-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

: 302840-48-8
methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

Guidance literature:: With dmap; In N,N-dimethyl-formamide; at 20 ℃; for 48h;
DOI:10.1016/S0040-4039(00)01107-2

Reference yield:

: 302840-41-1
(+)-methyl (1R)-1,5,5-trimethyl-6-methylenecyclohex-3-en-2-one-1-acetate

: 302840-48-8
methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

Guidance literature:: Multi-step reaction with 5 steps

1: 90 percent / H₂ / Pd/C / ethyl acetate / 0.5 h

2: NaOH / methanol; H₂O / 12 h / Heating

3: NaBH₄ / tetrahydrofuran / 3 h / 0 °C

4: diethyl ether / 0.17 h / 0 °C

5: 95 percent / DMAP / dimethylformamide / 48 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; 1: Catalytic hydrogenation / 2: Hydrolysis / 3: Hydrogenation / 4: Esterification / 5: Etherification;
DOI:10.1016/S0040-4039(00)01107-2

Reference yield:

: (1R,4R,8R)-8-Hydroperoxy-8-methoxy-1,5,5-trimethyl-6-methylene-bicyclo[2.2.2]octan-2-one

: 302840-48-8
methyl 2-[(1R,2R)-2-(tert-butyldimethylsilyloxy)-1,5,5-trimethyl-6-methylenecyclohexyl]acetate

Guidance literature:: Multi-step reaction with 6 steps

1: Ac₂O; NEt₃; DMAP / benzene / 6 h / Heating

2: 90 percent / H₂ / Pd/C / ethyl acetate / 0.5 h

3: NaOH / methanol; H₂O / 12 h / Heating

4: NaBH₄ / tetrahydrofuran / 3 h / 0 °C

5: diethyl ether / 0.17 h / 0 °C

6: 95 percent / DMAP / dimethylformamide / 48 h / 20 °C

With dmap; sodium hydroxide; sodium tetrahydroborate; hydrogen; acetic anhydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; water; ethyl acetate; N,N-dimethyl-formamide; benzene; 1: Criegee fragmentation / 2: Catalytic hydrogenation / 3: Hydrolysis / 4: Hydrogenation / 5: Esterification / 6: Etherification;
DOI:10.1016/S0040-4039(00)01107-2