{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

Base Information

Chemical Name:{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol
CAS No.:221290-60-4
Molecular Formula:C₁₈H₃₂O₄
Molecular Weight:312.45
Hs Code.:

Synonyms:{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

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Chemical Property of {(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

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Technology Process of {(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

There total 11 articles about {(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol 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:

: 221290-58-0
(Z)-4-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enyl]-2-methyl-but-2-en-1-ol

: 221290-60-4
{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

: 221290-61-5
{(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: With titanium(IV) isopropylate; tert.-butylhydroperoxide; (-)-diethyl tartrate; In dichloromethane; at -20 ℃; Yield given; Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1016/S0040-4039(98)80045-2

Reference yield:

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

: 221290-60-4
{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 9 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

5.1: 98 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

6.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / 20 °C

7.1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C

8.1: 92 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

9.1: (-)-diethyltartrate; 3 Angstroem molecular sieves; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 18 h / -20 °C

With tert.-butylhydroperoxide; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; n-butyllithium; 3 A molecular sieve; L-Selectride; sodium hydride; Dess-Martin periodane; (-)-diethyl tartrate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; titanium(IV) isopropylate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; xylene; 4.1: Ireland-Claisen rearrangement / 4.2: Ireland-Claisen rearrangement / 4.3: Ireland-Claisen rearrangement / 7.1: Horner-Emmons reaction;
DOI:10.1016/S0040-4020(01)00739-6

Reference yield:

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

: 221290-60-4
{(2R,3S)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

Guidance literature:: Multi-step reaction with 3 steps

1: NaH / 1,2-dimethoxy-ethane / 1 h / 20 °C

2: 92 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

3: (-)-diethyltartrate; 3 Angstroem molecular sieves; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 18 h / -20 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; 3 A molecular sieve; sodium hydride; (-)-diethyl tartrate; titanium(IV) isopropylate; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; 1: Horner-Emmons reaction;
DOI:10.1016/S0040-4020(01)00739-6