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

Base Information

Chemical Name:(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)hexane
CAS No.:263138-25-6
Molecular Formula:C₂₄H₄₄O₅Si
Molecular Weight:440.696
Hs Code.:

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

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

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

There total 5 articles about (2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-6-(4-methoxybenzyl)oxy-3-(methoxymethoxy)hexane 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: 90.0%

: 824-94-2
p-methoxybenzyl chloride

: 263138-24-5
(2S,3R,4R)-1-(tert-butyldimethylsilyl)oxy-2,4-dimethyl-3-(methoxymethoxy)hexan-6-ol

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

Guidance literature:: With 15-crown-5; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃; for 120h;
DOI:10.1021/jo991689x

Reference yield:

: 104701-87-3
(2S)-3-(tert-butyl-dimethyl-silyloxy)-2-methyl-propanal

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 79 percent / PdCl₂(dppf)-CH₂Cl₂; indium(I) iodide; triphenylphosphine / tetrahydrofuran; hexamethylphosphoric acid triamide / 0.5 h / 20 °C

2.1: 96 percent / i-Pr₂NEt; Bu₄NI / CH₂Cl₂ / 48 h / 20 °C

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

3.2: 75 percent / H₂O₂; NaOH / H₂O; 1,2-dimethoxy-ethane / 0.5 h

4.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h

5.1: 90 percent / NaH; 15-crown-5; Bu₄NI / tetrahydrofuran / 120 h / 20 °C

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; indium iodide; 15-crown-5; bis(cyclohexanyl)borane; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; hexane; dichloromethane; 1.1: Condensation / 2.1: Etherification / 3.1: Addition / 3.2: Oxidation / 4.1: Reduction / 5.1: Etherification;
DOI:10.1021/jo991689x

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 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

With 15-crown-5; bis(cyclohexanyl)borane; 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;
DOI:10.1021/jo991689x