(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

Base Information

Chemical Name:(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene
CAS No.:107173-28-4
Molecular Formula:C₂₄H₄₀O₂Si
Molecular Weight:388.666
Hs Code.:

Synonyms:(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

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Chemical Property of (3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

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Technology Process of (3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

There total 7 articles about (3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene 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:

: 107173-24-0
(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentanal

: 107173-28-4
(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h

2: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature

3: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min

With n-butyllithium; 1,10-Phenanthroline; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether;
DOI:10.1021/jo00383a012

Reference yield:

: 107173-23-9
(2S,4S)-5-<(tert-butyldimethylsilyl)oxy>-2,4-dimethyl-pentan-1-ol

: 107173-28-4
(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

Guidance literature:: Multi-step reaction with 4 steps

1: 91 percent / oxalyl chloride, Me₂SO / CH₂Cl₂ / 0.75 h / -78 °C

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 25 min, 2.) THF, hexane, -78 deg C, 1.5 h

3: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature

4: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min

With n-butyllithium; 1,10-Phenanthroline; oxalyl dichloride; dimethyl sulfoxide; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether; dichloromethane;
DOI:10.1021/jo00383a012

Reference yield:

: 101032-70-6,101143-49-1,105928-39-0,105928-40-3,107173-25-1,107173-26-2
(6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethylnon-1-en-3-yn-5-ol

: 107173-28-4
(3E)-(5S,6S,8S)-9-<(tert-butyldimethylsilyl)oxy>-6,8-dimethyl-5-(benzyloxy)-1,3-nonadiene

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / Red-Al / diethyl ether / 1 h / Ambient temperature

2: 1.) 1,10-phenanthroline, n-BuLi / 1.) THF, hexane, -78 deg C, 2.) THF, hexane, HMPA, -78 deg C, 5 min

With n-butyllithium; 1,10-Phenanthroline; sodium bis(2-methoxyethoxy)aluminium dihydride; In diethyl ether;
DOI:10.1021/jo00383a012