[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

Base Information

Chemical Name:[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate
CAS No.:925212-41-5
Molecular Formula:C₂₄H₄₄O₄Si
Molecular Weight:424.696
Hs Code.:

Synonyms:[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

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Chemical Property of [5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

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Technology Process of [5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

There total 1 articles about [5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl 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: 80.0%

: 61362-77-4
5-[tert-butyldimethylsilyloxy]pent-1-yne

: 144067-40-3
Acetic acid 5-formyl-2,6,6-trimethyl-cyclohex-1-enylmethyl ester

: 925212-41-5
[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

Guidance literature:: 5-[tert-butyldimethylsilyloxy]pent-1-yne; With Schwartz's reagent; In dichloromethane; for 0.25h;

Acetic acid 5-formyl-2,6,6-trimethyl-cyclohex-1-enylmethyl ester; With silver perchlorate; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/j.tet.2006.10.058

Reference yield: 95.0%

: 925212-41-5
[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

: 3970-21-6
2-Methoxyethoxymethyl chloride

: 925212-68-6
acetic acid 5-[6-(tert-butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethoxymethoxy)-hex-2-enyl]-2,6,6-trimethyl-cyclohex-1-enylmethyl ester

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 14h;
DOI:10.1016/j.tet.2006.10.058

Reference yield:

: 925212-41-5
[5-((E)-6-[tert-butyldimethylsilyloxy]-1-hydroxy-2-hexenyl)-2,6,6-trimethyl-1-cyclohexenyl]methyl acetate

: (E)-7-(3-acetyl-2,2,4-trimethyl-3-cyclohexenyl)-7-[(2-methoxyethoxy)methoxy]-5-hepten-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 95 percent / diisopropylethylamine; DMAP / CH₂Cl₂ / 14 h / 20 °C

2: 90 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

3: 85 percent / LiOH*H₂O / H₂O; methanol / 1 h / 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 1.08 h / 0 - 20 °C

5: 50 mg / tetrahydrofuran / 1 h / 20 °C

6: 3.7 mg / Grubbs' II catalyst / CH₂Cl₂ / 12 h / Heating

With dmap; lithium hydroxide; tetrabutyl ammonium fluoride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/j.tet.2006.10.058