[(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

Base Information

Chemical Name:[(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid
CAS No.:1026434-75-2
Molecular Formula:C₂₀H₃₆O₃Si
Molecular Weight:352.59
Hs Code.:

Synonyms:

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Chemical Property of [(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

Chemical Property:

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Technology Process of [(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

There total 24 articles about [(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-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:

: [(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetaldehyde

: 1026434-75-2
[(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In tert-butyl alcohol; at 20 ℃;

Reference yield:

: 128355-20-4
(3R,4S)-3-tert-butyloxycarbonylmethyl-4-hydroxy-5-tetrahydropyranyloxypentanoic acid γ-lactone

: 1026434-75-2
[(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

Guidance literature:: Multi-step reaction with 25 steps

1.1: 87 percent / DIBALH / tetrahydrofuran / -78 °C

2.1: 99 percent / (+/-)-CSA / 50 °C

3.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

4.1: LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

6.1: TBAF / tetrahydrofuran / 20 °C

7.1: Et₃N / CH₂Cl₂ / 0 °C

8.1: NaI / acetone / Heating

9.1: BuLi / tetrahydrofuran / -78 - 20 °C

9.2: tetrahydrofuran / -78 - 20 °C

10.1: (+/-)-CSA / methanol; H₂O / 60 °C

11.1: 72 percent / diethyl ether / -78 °C

12.1: aq. AcOH / 60 °C

13.1: 1,2-dichloro-ethane / 80 °C

14.1: 68 percent / Et₃N; DMAP / dimethylformamide / 40 °C

15.1: 87 percent / PDC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

16.1: 81 percent / NaBH₄ / methanol / 0 °C

17.1: CBr₄; Ph₃P / CH₂Cl₂ / 20 °C

18.1: 55 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

19.1: 78 percent / DIBALH / diethyl ether / -78 °C

20.1: Bu₃P; pyridine / 20 °C

21.1: MCPBA / CH₂Cl₂

22.1: i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

23.1: 95 percent / Na; NH₃ / tetrahydrofuran / -78 °C

24.1: PDC; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 20 °C

25.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With pyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; samarium diiodide; 2-methyl-but-2-ene; carbon tetrabromide; tributylphosphine; 4 A molecular sieve; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; tert-butyl alcohol; 13.1: Wittig reaction;

Reference yield:

: 561063-79-4
[(2S,3R)-5-Hydroxy-2-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furan-3-yl]-acetic acid tert-butyl ester

: 1026434-75-2
[(1R,2R,4S,5S)-2-(tert-Butyl-dimethyl-silanyloxy)-5-isopropenyl-4-methyl-4-vinyl-cyclohexyl]-acetic acid

Guidance literature:: Multi-step reaction with 24 steps

1.1: 99 percent / (+/-)-CSA / 50 °C

2.1: Et₃N; DMAP / dimethylformamide / 0 - 20 °C

3.1: LiAlH₄ / diethyl ether / 0 - 20 °C

4.1: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

5.1: TBAF / tetrahydrofuran / 20 °C

6.1: Et₃N / CH₂Cl₂ / 0 °C

7.1: NaI / acetone / Heating

8.1: BuLi / tetrahydrofuran / -78 - 20 °C

8.2: tetrahydrofuran / -78 - 20 °C

9.1: (+/-)-CSA / methanol; H₂O / 60 °C

10.1: 72 percent / diethyl ether / -78 °C

11.1: aq. AcOH / 60 °C

12.1: 1,2-dichloro-ethane / 80 °C

13.1: 68 percent / Et₃N; DMAP / dimethylformamide / 40 °C

14.1: 87 percent / PDC; 4 Angstroem molecular sieves / CH₂Cl₂ / 20 °C

15.1: 81 percent / NaBH₄ / methanol / 0 °C

16.1: CBr₄; Ph₃P / CH₂Cl₂ / 20 °C

17.1: 55 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

18.1: 78 percent / DIBALH / diethyl ether / -78 °C

19.1: Bu₃P; pyridine / 20 °C

20.1: MCPBA / CH₂Cl₂

21.1: i-Pr₂NEt / 1,2-dichloro-benzene / 160 °C

22.1: 95 percent / Na; NH₃ / tetrahydrofuran / -78 °C

23.1: PDC; 4 Angstroem molecular sieves / 1,2-dichloro-ethane / 20 °C

24.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

With pyridine; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; samarium diiodide; 2-methyl-but-2-ene; carbon tetrabromide; tributylphosphine; 4 A molecular sieve; 10-camphorsufonic acid; tetrabutyl ammonium fluoride; ammonia; sodium; sodium hydride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; sodium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1,2-dichloro-benzene; acetone; tert-butyl alcohol; 12.1: Wittig reaction;