Cyclohexanone, 3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-2,4-dihydroxy-4-(hydroxymethyl)-, (2S,3S,4R)-

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Chemical Name:Cyclohexanone, 3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-2,4-dihydroxy-4-(hydroxymethyl)-, (2S,3S,4R)-
CAS No.:877052-54-5
Molecular Formula:C15H24O4
Molecular Weight:268.353
Hs Code.:

Synonyms:

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Chemical Property of Cyclohexanone, 3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-2,4-dihydroxy-4-(hydroxymethyl)-, (2S,3S,4R)-

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Technology Process of Cyclohexanone, 3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-2,4-dihydroxy-4-(hydroxymethyl)-, (2S,3S,4R)-

There total 9 articles about Cyclohexanone, 3-[(1E)-1,5-dimethyl-1,4-hexadienyl]-2,4-dihydroxy-4-(hydroxymethyl)-, (2S,3S,4R)- 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: 74.0%

: 877052-53-4
(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-4-trimethylsilanyloxy-cyclohex-3-enol

: 877052-54-5
(2S,3S,4R)-3-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,4-dihydroxy-4-hydroxymethyl-cyclohexanone

Guidance literature:: (1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-4-trimethylsilanyloxy-cyclohex-3-enol; With 3,3-dimethyldioxirane; In acetone; at -90 ℃;

With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1002/anie.200502826

Reference yield:

: 682746-13-0
(R)-7-(N-phenyl-aminooxy)-2,3-dioxa-spiro[4.5]decan-8-one

: 877052-54-5
(2S,3S,4R)-3-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,4-dihydroxy-4-hydroxymethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 9 steps

1.1: 90 percent / H₂ / Pd/C / tetrahydrofuran / 3 h

2.1: 68 percent / Et₃N / 2.5 h / 0 °C

3.1: 72 percent / DIBAL-H / diethyl ether / -60 - -30 °C

4.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -50 - -30 °C

5.1: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C

6.1: Et₃N; DMAP / CH₂Cl₂

7.1: t-BuLi; Me₂Zn / tetrahydrofuran

7.2: tetrahydrofuran / 2 h / -78 - -40 °C

8.1: Et₃N / tetrahydrofuran / 1 h / -40 - -20 °C

9.1: dimethyldioxirane / acetone / -90 °C

9.2: 74 percent / TBAF / tetrahydrofuran

With dmap; Amberlyst 15; hydrogen; dimethyl zinc(II); tert.-butyl lithium; 3,3-dimethyldioxirane; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 7.2: Michael addition;
DOI:10.1002/anie.200502826

Reference yield:

: 851764-31-3
(R)-4-hydroxy-1,4-dioxa-spiro[4.5]decan-8-one

: 877052-54-5
(2S,3S,4R)-3-((E)-1,5-Dimethyl-hexa-1,4-dienyl)-2,4-dihydroxy-4-hydroxymethyl-cyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 68 percent / Et₃N / 2.5 h / 0 °C

2.1: 72 percent / DIBAL-H / diethyl ether / -60 - -30 °C

3.1: DIBAL-H / CH₂Cl₂ / 0.33 h / -50 - -30 °C

4.1: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C

5.1: Et₃N; DMAP / CH₂Cl₂

6.1: t-BuLi; Me₂Zn / tetrahydrofuran

6.2: tetrahydrofuran / 2 h / -78 - -40 °C

7.1: Et₃N / tetrahydrofuran / 1 h / -40 - -20 °C

8.1: dimethyldioxirane / acetone / -90 °C

8.2: 74 percent / TBAF / tetrahydrofuran

With dmap; Amberlyst 15; dimethyl zinc(II); tert.-butyl lithium; 3,3-dimethyldioxirane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 6.2: Michael addition;
DOI:10.1002/anie.200502826