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

Base Information

Chemical Name:(2R,3R,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexane
CAS No.:910043-07-1
Molecular Formula:C₃₀H₃₈O₃Si
Molecular Weight:474.715
Hs Code.:

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

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Chemical Property of (2R,3R,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexane

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Technology Process of (2R,3R,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexane

There total 3 articles about (2R,3R,5S)-1-(benzyloxy)-6-(tert-butyldiphenylsilyloxy)-2,3-epoxy-5-methylhexane 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:

: 100-39-0
benzyl bromide

: 136262-55-0
(2E,5S)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-en-1-ol

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

Guidance literature:: (2E,5S)-6-(tert-butyldiphenylsilyloxy)-5-methylhex-2-en-1-ol; With tert.-butylhydroperoxide; (-)-diethyl tartrate; titanium(IV) isopropylate; In dichloromethane; at -40 - -23 ℃; for 24h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; potassium hydride; In tetrahydrofuran; at 0 - 20 ℃; for 0.75h;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 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

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