(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

Base Information

Chemical Name:(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol
CAS No.:849122-67-4
Molecular Formula:C₁₉H₃₄O₃
Molecular Weight:310.477
Hs Code.:

Synonyms:(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

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Technology Process of (2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

There total 1 articles about (2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol 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: 85.0%

: 21969-32-4,6088-88-6
(1-methylallyl)magnesium chloride

: 221290-57-9
[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetaldehyde

: 849122-67-4
(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

Guidance literature:: (1-methylallyl)magnesium chloride; With (S,S)-taddol(cyclopentadienyl)TiCl; In tetrahydrofuran; diethyl ether; at -78 - 0 ℃;

[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetaldehyde; In tetrahydrofuran; diethyl ether; at -78 ℃; for 15h;
DOI:10.1016/j.tet.2004.12.039

Reference yield: 82.0%

: 849122-67-4
(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

: 107-30-2
chloromethyl methyl ether

: 849122-68-5
(4R,5R,6R)-5-dimethoxymethyl-4-isopropyl-6-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-1-methyl-cyclohexene

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 15h;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: 849122-67-4
(2S,3R)-1-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-3-methyl-pent-4-en-2-ol

: 849122-73-2
(S)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enyl}-pent-4-en-2-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / DIPEA; TBAI / CH₂Cl₂ / 15 h / 20 °C

2: LiBF₄ / acetonitrile; H₂O / 1 h / 20 °C

3: 505 mg / NaBH₄ / ethanol / 0.33 h / 20 °C

4: 100 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

5: 91 percent / 18-crown-6 / acetonitrile / 8 h / 80 °C

6: DIBAL-H / toluene; hexane / 0.75 h / -78 °C

7: tetrahydrofuran; diethyl ether / 23 h / -78 - -20 °C

With sodium tetrahydroborate; lithium tetrafluoroborate; 18-crown-6 ether; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; acetonitrile; 7: Brown allylation;
DOI:10.1016/j.tet.2004.12.039