benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

Base Information

Chemical Name:benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether
CAS No.:136786-39-5
Molecular Formula:C₃₃H₄₆O₄Si
Molecular Weight:534.811
Hs Code.:

Synonyms:benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

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Chemical Property of benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

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Technology Process of benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

There total 7 articles about benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether 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: 89.0%

: 136786-36-2
(2S,3S,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-2-ol

: 107-30-2
chloromethyl methyl ether

: 136786-39-5
benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

Guidance literature:: With tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 48h;
DOI:10.1021/ja0581346

Reference yield:

: 910043-29-7
(2S,4E)-6-[(4-methoxyphenyl)methoxy]-2-methylhex-4-en-1-ol

: 136786-39-5
benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 15 h / 20 °C

1.2: DDQ; water / CH₂Cl₂ / 0.25 h / 20 °C

1.3: 72 percent / NaBH₄ / CH₂Cl₂ / 24 h / 20 °C

2.1: (-)-DET; tBuOOH; 4A MS / Ti(OiPr)4 / CH₂Cl₂ / 24 h / -40 - -23 °C

2.2: 2.42 g / KH; TBAI / tetrahydrofuran / 0.75 h / 0 - 20 °C

3.1: 78 percent / nBuLi / petroleum ether / 3 h / -30 - 0 °C

4.1: 89 percent / iPr₂NEt; TBAI / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; n-butyllithium; tetra-(n-butyl)ammonium iodide; (-)-diethyl tartrate; N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; In dichloromethane; N,N-dimethyl-formamide; Petroleum ether;
DOI:10.1021/ja0581346

Reference yield:

: (1S,4R)-2-[(2S,4E)-6-[(p-methoxyphenyl)methoxy]-2-methylhex-4-enoyl]-1,7,7-trimethyl-2-azabicyclo[2.2.1]heptan-3-one

: 136786-39-5
benzyl [6-(tert-butyldiphenylsilyloxy)-3(S),5(S)-dimethyl-2(S)-(methoxymethoxy)hex-1-yl] ether

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / LiAlH₄ / diethyl ether / 2 h / 0 - 8 °C

2.1: imidazole / dimethylformamide / 15 h / 20 °C

2.2: DDQ; water / CH₂Cl₂ / 0.25 h / 20 °C

2.3: 72 percent / NaBH₄ / CH₂Cl₂ / 24 h / 20 °C

3.1: (-)-DET; tBuOOH; 4A MS / Ti(OiPr)4 / CH₂Cl₂ / 24 h / -40 - -23 °C

3.2: 2.42 g / KH; TBAI / tetrahydrofuran / 0.75 h / 0 - 20 °C

4.1: 78 percent / nBuLi / petroleum ether / 3 h / -30 - 0 °C

5.1: 89 percent / iPr₂NEt; TBAI / CH₂Cl₂ / 48 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; n-butyllithium; tetra-(n-butyl)ammonium iodide; (-)-diethyl tartrate; N-ethyl-N,N-diisopropylamine; titanium(IV) isopropylate; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; Petroleum ether;
DOI:10.1021/ja0581346