(2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde

Base Information

• Chemical Name: (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde
• CAS No.: 913093-95-5
• Molecular Formula: C₃₁H₄₄O₅Si
• Molecular Weight: 524.773

Synonyms:

Chemical Property of (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde

There total 20 articles about (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde 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:

(1R,3R,5R)-5-isopropenyl-2,2-dimethyl-1-vinylcyclohexane-1,3-diol (913093-74-0) → (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde (913093-95-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂

2.1: 9.5 g / CrO₃; aq. H₂SO₄ / acetone / 0.33 h / 0 °C

3.1: 91 percent / K₂CO₃ / acetonitrile / 2 h

4.1: 92 percent / naphthalenesulfonic acid / CH₂Cl₂ / 2 h

5.1: t-BuOK / tetrahydrofuran / 0.17 h / -78 °C

5.2: 97 percent / tetrahydrofuran / 1 h / -78 °C

6.1: 94 percent / NaIO₄ / methanol; H₂O

7.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1 h / 0 °C

7.2: K₂CO₃ / tetrahydrofuran; H₂O

8.1: 5.54 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.33 h / 0 °C

9.1: ozone / methanol / -78 °C

9.2: Cu(Ac)2*H₂O / methanol / 0.17 h / 0 °C

9.3: 77 percent / FeSO₄*7H₂O / methanol / 1.67 h / 0 °C

10.1: tetrahydrofuran / 1 h / 0 °C

11.1: 4.27 g / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

12.1: SOCl₂; pyridine / CH₂Cl₂ / 0.5 h / -20 °C

13.1: Al₂O₃ / H₂O

14.1: imidazole / dimethylformamide

15.1: ozone / methanol / -78 °C

15.2: PPh₃ / methanol / 0.17 h

16.1: tetrahydrofuran / 1 h / -78 °C

17.1: K₂CO₃ / methanol / 1 h

18.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

19.1: NEt₃ / toluene

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; thionyl chloride; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic anhydride; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: Jones oxidation / 19.1: Wittig reaction;

DOI:10.1002/ejoc.200600284

Reference yield:

2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone (97643-04-4) → (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde (913093-95-5)

Guidance literature:

Multi-step reaction with 20 steps

1.1: BuLi / hexane; tetrahydrofuran / 1 h / -78 °C

1.2: 96 percent / tetrahydrofuran; hexane / 1 h / -78 - 0 °C

2.1: tert-butyl hydroperoxide / vanadylacetylacetonate / CH₂Cl₂

3.1: 9.5 g / CrO₃; aq. H₂SO₄ / acetone / 0.33 h / 0 °C

4.1: 91 percent / K₂CO₃ / acetonitrile / 2 h

5.1: 92 percent / naphthalenesulfonic acid / CH₂Cl₂ / 2 h

6.1: t-BuOK / tetrahydrofuran / 0.17 h / -78 °C

6.2: 97 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 94 percent / NaIO₄ / methanol; H₂O

8.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1 h / 0 °C

8.2: K₂CO₃ / tetrahydrofuran; H₂O

9.1: 5.54 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.33 h / 0 °C

10.1: ozone / methanol / -78 °C

10.2: Cu(Ac)2*H₂O / methanol / 0.17 h / 0 °C

10.3: 77 percent / FeSO₄*7H₂O / methanol / 1.67 h / 0 °C

11.1: tetrahydrofuran / 1 h / 0 °C

12.1: 4.27 g / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

13.1: SOCl₂; pyridine / CH₂Cl₂ / 0.5 h / -20 °C

14.1: Al₂O₃ / H₂O

15.1: imidazole / dimethylformamide

16.1: ozone / methanol / -78 °C

16.2: PPh₃ / methanol / 0.17 h

17.1: tetrahydrofuran / 1 h / -78 °C

18.1: K₂CO₃ / methanol / 1 h

19.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

20.1: NEt₃ / toluene

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; n-butyllithium; thionyl chloride; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic anhydride; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Jones oxidation / 20.1: Wittig reaction;

DOI:10.1002/ejoc.200600284

Reference yield:

(3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone (913093-76-2) → (2E)-3-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-6,6,8-trimethyl-7-(3-methyl-2-oxobut-3-en-1-yl)-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-4-yl}acrylaldehyde (913093-95-5)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 91 percent / K₂CO₃ / acetonitrile / 2 h

2.1: 92 percent / naphthalenesulfonic acid / CH₂Cl₂ / 2 h

3.1: t-BuOK / tetrahydrofuran / 0.17 h / -78 °C

3.2: 97 percent / tetrahydrofuran / 1 h / -78 °C

4.1: 94 percent / NaIO₄ / methanol; H₂O

5.1: trifluoroacetic anhydride; pyridine / tetrahydrofuran / 1 h / 0 °C

5.2: K₂CO₃ / tetrahydrofuran; H₂O

6.1: 5.54 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.33 h / 0 °C

7.1: ozone / methanol / -78 °C

7.2: Cu(Ac)2*H₂O / methanol / 0.17 h / 0 °C

7.3: 77 percent / FeSO₄*7H₂O / methanol / 1.67 h / 0 °C

8.1: tetrahydrofuran / 1 h / 0 °C

9.1: 4.27 g / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

10.1: SOCl₂; pyridine / CH₂Cl₂ / 0.5 h / -20 °C

11.1: Al₂O₃ / H₂O

12.1: imidazole / dimethylformamide

13.1: ozone / methanol / -78 °C

13.2: PPh₃ / methanol / 0.17 h

14.1: tetrahydrofuran / 1 h / -78 °C

15.1: K₂CO₃ / methanol / 1 h

16.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

17.1: NEt₃ / toluene

With pyridine; 1H-imidazole; aluminum oxide; sodium periodate; thionyl chloride; naphthalenesulfonic acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 17.1: Wittig reaction;

DOI:10.1002/ejoc.200600284

upstream raw materials:

formylmethyltriphenylphosphonium chloride

(1R,3R,5R)-5-isopropenyl-2,2-dimethyl-1-vinylcyclohexane-1,3-diol

(3S,5S)-3-hydroxy-5-isopropenyl-2,2-dimethyl-3-[(2R)-oxiran-2-yl]cyclohexanone

(2S,4S,5S)-4-hydroxymethyl-6,6,8-trimethyl-2-phenyl-1,3-dioxaspiro[4.5]dec-8-en-7-one

Downstream raw materials:

1-{(2S,4S,5S,9S)-9-[tert-butyl(dimethyl)silyloxy]-4-[(1E)-3-hydroxyprop-1-en-1-yl]-6,6,8-trimethyl-2-phenyl-1,3-dioxaspiro[4.5]dec-7-en-7-yl}-3-methylbut-3-en-2-one

2-{4-[(2S,4S,5S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-4-((E)-3-hydroxy-propenyl)-6,6,8-trimethyl-2-phenyl-1,3-dioxa-spiro[4.5]dec-7-en-7-yl]-2-methyl-3-oxo-butyl}-malonic acid dimethyl ester

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