(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Base Information

Chemical Name:(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol
CAS No.:1392307-52-6
Molecular Formula:C₂₆H₄₄O₃Si
Molecular Weight:432.719
Hs Code.:

Synonyms:(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

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Chemical Property of (4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

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Technology Process of (4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

There total 7 articles about (4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-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: 85.0%

: 1392307-51-5
(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

: 1392307-52-6
(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; toluene; at -40 ℃; Inert atmosphere;
DOI:10.1002/anie.201108223

Reference yield:

: 1392307-50-4
(2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol

: 1392307-52-6
(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

2: dichloromethane / 20 h

3: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

With diisobutylaluminium hydride; Dess-Martin periodane; In diethyl ether; dichloromethane; toluene; 1: Dess-Martin oxidation / 2: Wittig reaction;
DOI:10.1002/anie.201108223

Reference yield:

: (S)-4-benzyl-3-((2S,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-enoyl)oxazolidin-2-one

: 1392307-52-6
(4R,5R,6R,(E))-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dien-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1: sodium tetrahydroborate / tetrahydrofuran; water / 0 - 20 °C

2: Dess-Martin periodane / dichloromethane / 2.5 h / 20 °C

3: dichloromethane / 20 h

4: diisobutylaluminium hydride / diethyl ether; toluene / -40 °C / Inert atmosphere

With sodium tetrahydroborate; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; diethyl ether; dichloromethane; water; toluene; 2: Dess-Martin oxidation / 3: Wittig reaction;
DOI:10.1002/anie.201108223