(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

Base Information

Chemical Name:(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde
CAS No.:380414-35-7
Molecular Formula:C₁₈H₃₀O₄
Molecular Weight:310.434
Hs Code.:

Synonyms:(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

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Chemical Property of (2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

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Technology Process of (2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

There total 10 articles about (2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde 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: 98.0%

: 221290-72-8
{(2R,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxiranyl}-methanol

: 380414-35-7
(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; Ambient temperature;
DOI:10.1016/S0040-4039(98)80045-2

Reference yield:

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

: 380414-35-7
(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

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

2: 72 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

3: 43 percent / (-)-diethyltartrate; 3 Angstroem molecular sieves; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 18 h / -20 °C

4: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With tert.-butylhydroperoxide; lithium aluminium tetrahydride; 3 A molecular sieve; sodium hydride; Dess-Martin periodane; (-)-diethyl tartrate; titanium(IV) isopropylate; In 1,2-dimethoxyethane; diethyl ether; dichloromethane; 1: Horner-Emmons reaction / 4: Wittig reaction;
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

: 380414-35-7
(2S,3R)-3-[(1R,5R,6R)-6-dimethoxymethyl-5-isopropyl-2-methyl-cyclohex-2-enylmethyl]-2-methyl-oxirane-2-carbaldehyde

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: xylene / 5 h / 190 °C

2.2: 2.0 M NaOH / tetrahydrofuran / 3 h / 20 °C

2.3: 82 percent / 10 percent aq. HCl / H₂O / 20 °C / pH 3

3.1: 98 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 20 °C

4.1: 97 percent / Dess-Martin periodinane / CH₂Cl₂ / 30 h / 20 °C

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

6.1: 72 percent / LiAlH₄ / diethyl ether / 1 h / 0 - 20 °C

7.1: 43 percent / (-)-diethyltartrate; 3 Angstroem molecular sieves; TBHP / Ti(Oi-Pr)4 / CH₂Cl₂ / 18 h / -20 °C

8.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

With tert.-butylhydroperoxide; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; lithium aluminium tetrahydride; n-butyllithium; 3 A molecular sieve; sodium hydride; Dess-Martin periodane; (-)-diethyl tartrate; 1,1,1,3,3,3-hexamethyl-disilazane; titanium(IV) isopropylate; In tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; dichloromethane; xylene; 2.1: Ireland-Claisen rearrangement / 2.2: Ireland-Claisen rearrangement / 2.3: Ireland-Claisen rearrangement / 5.1: Horner-Emmons reaction / 8.1: Wittig reaction;
DOI:10.1016/S0040-4020(01)00739-6