(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Base Information

Chemical Name:(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate
CAS No.:1246937-65-4
Molecular Formula:C₂₆H₃₇NO₄
Molecular Weight:427.584
Hs Code.:

Synonyms:(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

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Chemical Property of (3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

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Technology Process of (3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

There total 6 articles about (3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate 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: 55.0%

: 1189125-30-1
(S)-1-phenylhex-4-yn-3-ol

: 180779-81-1
(3R,4R,E)-2,4-dimethyl-7-oxo-7-(prop-2-ynylamino)hept-5-en-3-yl acetate

: C₂₆H₃₅NO₃

: 1246937-65-4
(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Guidance literature:: (S)-1-phenylhex-4-yn-3-ol; With triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride; In diethyl ether; hexane; at -78 - -30 ℃; for 2.5h; Inert atmosphere;

(3R,4R,E)-2,4-dimethyl-7-oxo-7-(prop-2-ynylamino)hept-5-en-3-yl acetate; In diethyl ether; hexane; at -78 - -30 ℃; for 13.5h; Inert atmosphere;

With water; ammonium chloride; In diethyl ether; hexane; at -30 - 20 ℃; Saturated solution;
DOI:10.1002/anie.201002220

Reference yield:

: 159420-55-0
C₆H₈N₂O₂

: C₂₆H₃₅NO₃

: 1246937-65-4
(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate) / pentane / 24 h / -75 °C / Molecular sieve; Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

3.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.2: 5 h / Inert atmosphere; Reflux

4.1: pyridine; dmap / dichloromethane / Inert atmosphere

5.1: triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride / diethyl ether; hexane / 1 h / -30 °C / Inert atmosphere

5.2: 12 h / -30 °C / Inert atmosphere

With pyridine; triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; dirhodium tetrakis(S-(N-dodecylbenzenesulfonyl)prolinate); trimethylaluminum; titanium tetrachloride; cyclopentylmagnesium chloride; In diethyl ether; hexane; dichloromethane; pentane; 5.2: Negishi coupling reaction;
DOI:10.1021/jo202119p

Reference yield:

: methyl (2S,3E)-2-(dimethyl(phenyl)silyl)pent-3-enoate

: C₂₆H₃₅NO₃

: 1246937-65-4
(3R,4R,E)-7-((S,2E,4E)-6-hydroxy-4-methyl-8-phenylocta-2,4-dienylamino)-2,4-dimethyl-7-oxohept-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 72 h / -20 °C / Inert atmosphere

2.1: trimethylaluminum / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.2: 5 h / Inert atmosphere; Reflux

3.1: pyridine; dmap / dichloromethane / Inert atmosphere

4.1: triisopropoxytitanium(IV) chloride; n-butyllithium; cyclopentylmagnesium chloride / diethyl ether; hexane / 1 h / -30 °C / Inert atmosphere

4.2: 12 h / -30 °C / Inert atmosphere

With pyridine; triisopropoxytitanium(IV) chloride; dmap; n-butyllithium; trimethylaluminum; titanium tetrachloride; cyclopentylmagnesium chloride; In diethyl ether; hexane; dichloromethane; 4.2: Negishi coupling reaction;
DOI:10.1021/jo202119p