(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

Base Information

Chemical Name:(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol
CAS No.:263138-26-7
Molecular Formula:C₁₈H₃₀O₅
Molecular Weight:326.433
Hs Code.:

Synonyms:(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

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Chemical Property of (2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

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Technology Process of (2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

There total 6 articles about (2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol 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: 71.0%

: 263138-25-6
(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)hexane

: 263138-26-7
(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;
DOI:10.1021/jo991689x

Reference yield:

: 263138-21-2
(2S,3R,4R)-(+)-1-(tert-butyldimethylsilyloxy)-2,4-dimethyl-5-hexyn-3-ol

: 263138-26-7
(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 96 percent / i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

2.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

2.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

3.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

4.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

5.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

With 15-crown-5; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; 1.1: Etherification / 2.1: Addition / 2.2: Oxidation / 3.1: Reduction / 4.1: Etherification / 5.1: Hydrolysis;
DOI:10.1021/jo991689x

Reference yield:

: 263138-22-3
(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-methoxymethoxy-5-hexyne

: 263138-26-7
(2S,3R,4R)-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)-1-hexanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: (c-C₆H₁₁)2BH / 1,2-dimethoxy-ethane / 6.5 h / 20 °C

1.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

2.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

3.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

4.1: 71 percent / Bu₄NF / tetrahydrofuran / 24 h / 20 °C

With 15-crown-5; bis(cyclohexanyl)borane; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 1.1: Addition / 1.2: Oxidation / 2.1: Reduction / 3.1: Etherification / 4.1: Hydrolysis;
DOI:10.1021/jo991689x