(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

Base Information

Chemical Name:(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene
CAS No.:171087-12-0
Molecular Formula:C₂₃H₄₀O₄Si
Molecular Weight:408.654
Hs Code.:

Synonyms:(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

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Chemical Property of (2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

Chemical Property:

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Technology Process of (2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

There total 9 articles about (2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene 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: 91.0%

: 107-30-2
chloromethyl methyl ether

: 171087-11-9
(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-2-octen-5-ol

: 171087-12-0
(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 12h; Ambient temperature;

Reference yield:

: 161275-75-8
(2R)-6-(tetrahydro-2H-pyran-2-yloxy)hex-4-yn-2-ol

: 171087-12-0
(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

Guidance literature:: Multi-step reaction with 9 steps

1: 86 percent / NaH, n-Bu₄NI / paraffin; tetrahydrofuran / 1.) 0 deg C, 30 min; room temperature, 1 h, 2.) overnight

2: 95 percent / p-TsOH*H₂O / methanol / 3 h / Ambient temperature

3: 88 percent / LiAlH₄ / tetrahydrofuran / 3 h / Ambient temperature

4: 83 percent / Ti(OisoPr)4, 4A MC, L-(+)-diethyl tatrate, tert-butyl hydroperoxide / CH₂Cl₂; toluene / 5 h / -25 °C

5: Dess-Martin reagent / CH₂Cl₂ / 1 h / Ambient temperature

6: 89 percent / NaH / paraffin; tetrahydrofuran / 1.) 0 deg C, 30 min; room temperature, 1 h, 2.) -78 deg C, 2 h

7: 70 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

8: 89 percent / Et₃N, dimethylaminopyridine / CH₂Cl₂ / 6 h / Ambient temperature

9: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; diethyl (2R,3R)-tartrate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; paraffin;

Reference yield:

: 171087-07-3
(2S,3S,5R)-5-benzyloxy-2,3-epoxyhexan-1-ol

: 171087-12-0
(2E,5R,7R)-7-benzyloxy-1-(tert-butyldimethylsilyloxy)-5-methoxymethoxy-2-octene

Guidance literature:: Multi-step reaction with 5 steps

1: Dess-Martin reagent / CH₂Cl₂ / 1 h / Ambient temperature

2: 89 percent / NaH / paraffin; tetrahydrofuran / 1.) 0 deg C, 30 min; room temperature, 1 h, 2.) -78 deg C, 2 h

3: 70 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

4: 89 percent / Et₃N, dimethylaminopyridine / CH₂Cl₂ / 6 h / Ambient temperature

5: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / Ambient temperature

With dmap; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; paraffin;