[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

Base Information

Chemical Name:[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid
CAS No.:221290-56-8
Molecular Formula:C₁₅H₂₆O₄
Molecular Weight:270.369
Hs Code.:

Synonyms:[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

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Chemical Property of [(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

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Technology Process of [(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

There total 5 articles about [(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-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: 82.0%

: tert-Butyl-[1-((1S,4R,5R)-4-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyloxy)-vinyloxy]-dimethyl-silane

: 221290-56-8
[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

Guidance literature:: tert-Butyl-[1-((1S,4R,5R)-4-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyloxy)-vinyloxy]-dimethyl-silane; In xylene; at 190 ℃; for 5h;

With sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 3h;

With hydrogenchloride; In water; at 20 ℃; pH=3;
DOI:10.1016/S0040-4020(01)00739-6

Reference yield:

: 221290-71-7
acetic acid (1S,4R,5R)-4-dimethoxymethyl-5-isopropyl-2-methylcyclohex-2-enyl ester

: 221290-56-8
[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

Guidance literature:: With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium hydroxide; tert-butyldimethylsilyl chloride; lithium hexamethyldisilazane; Yield given; Multistep reaction; 1.) THF, -78 deg C to r.t.; 2.) xylene, 190 deg C, 5 h; 3.) THF;
DOI:10.1016/S0040-4039(98)80045-2

Reference yield:

: 221290-54-6
(4R,5R)-4-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enone

: 221290-56-8
[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-acetic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: 70 percent / tri-sec-butylborohydride (L-Selectide) / tetrahydrofuran / 0.67 h / -78 °C

2.1: 95 percent / triethylamine; dimethylaminopyridine / CH₂Cl₂ / 3 h / 25 °C

3.1: HN(TMS)2; n-BuLi; DMPU / tetrahydrofuran / 0.75 h / -78 - 20 °C

4.1: xylene / 5 h / 190 °C

4.2: 2.0 M NaOH / tetrahydrofuran / 3 h / 20 °C

4.3: 82 percent / 10 percent aq. HCl / H₂O / 20 °C / pH 3

With dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; n-butyllithium; L-Selectride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; dichloromethane; xylene; 4.1: Ireland-Claisen rearrangement / 4.2: Ireland-Claisen rearrangement / 4.3: Ireland-Claisen rearrangement;
DOI:10.1016/S0040-4020(01)00739-6