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

Base Information

Chemical Name:(4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate
CAS No.:1392307-51-5
Molecular Formula:C₂₈H₄₆O₄Si
Molecular Weight:474.756
Hs Code.:

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

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Chemical Property of (4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

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Technology Process of (4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate

There total 7 articles about (4R,5R,6R,(E))-ethyl 4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-6,10-dimethylundeca-2,9-dienoate 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: 82.0%

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

: 1099-45-2
ethyl (triphenylphosphoranylidene)acetate

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

Guidance literature:: (2R,3R,4R)-2-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-4,8-dimethylnon-7-en-1-ol; With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 2.5h;

ethyl (triphenylphosphoranylidene)acetate; In dichloromethane; at 20 ℃; for 20h;
DOI:10.1039/c3ob40692j

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

3: dichloromethane / 20 h

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 4 steps

1: 2,4,6-trimethyl-pyridine / dichloromethane / 0 - 20 °C / Inert atmosphere

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

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

4: dichloromethane / 20 h

With 2,4,6-trimethyl-pyridine; sodium tetrahydroborate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; 3: Dess-Martin oxidation / 4: Wittig reaction;
DOI:10.1002/anie.201108223