acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

Base Information

Chemical Name:acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester
CAS No.:634151-76-1
Molecular Formula:C₂₅H₄₂O₄
Molecular Weight:406.606
Hs Code.:

Synonyms:acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

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Chemical Property of acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

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Technology Process of acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

There total 9 articles about acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl 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: 80.0%

: 849122-74-3
(R)-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

: 108-24-7
acetic anhydride

: 634151-76-1
acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1016/j.tet.2004.12.039

Reference yield:

: (1R,2R,6R)-6-Isopropyl-2-((2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl)-3-methyl-cyclohex-3-enecarbaldehyde

: 634151-76-1
acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 505 mg / NaBH₄ / ethanol / 0.33 h / 20 °C

2: 100 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

3: 91 percent / 18-crown-6 / acetonitrile / 8 h / 80 °C

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

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

6: 80 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With dmap; sodium tetrahydroborate; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; toluene; acetonitrile; 5: Brown allylation;
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

: 634151-76-1
acetic acid (R)-1-{(1R,2R,6R)-6-isopropyl-2-[(2S,3R)-2-methoxymethoxy-3-methyl-pent-4-enyl]-3-methyl-cyclohex-3-enylmethyl}-but-3-enyl ester

Guidance literature:: Multi-step reaction with 8 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

8: 80 percent / Et₃N; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With dmap; 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