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

Base Information

Chemical Name:(2S,3S,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-2-ol
CAS No.:136786-36-2
Molecular Formula:C₃₁H₄₂O₃Si
Molecular Weight:490.758
Hs Code.:

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

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Chemical Property of (2S,3S,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-2-ol

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Technology Process of (2S,3S,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-2-ol

There total 4 articles about (2S,3S,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-2-ol 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: 78.0%

: 910043-07-1
(2R,3R,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexane

: 75-24-1
trimethylaluminum

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

Guidance literature:: With n-butyllithium; In Petroleum ether; at -30 - 0 ℃; for 3h;
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

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

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 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

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