(2E)-3-{(2S,4S,5S,9R)-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,9R)-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.: 913093-89-7
• Molecular Formula: C₃₁H₄₄O₅Si
• Molecular Weight: 524.773

Synonyms:(2E)-3-{(2S,4S,5S,9R)-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 of (2E)-3-{(2S,4S,5S,9R)-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,9R)-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 23 articles about (2E)-3-{(2S,4S,5S,9R)-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,9R)-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 (913093-89-7)

Guidance literature:

Multi-step reaction with 22 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: DIAD; PPh₃ / tetrahydrofuran

15.1: K₂CO₃ / methanol

16.1: NEt₃ / CH₂Cl₂

17.1: 92 percent / imidazole / dimethylformamide

18.1: ozone / methanol / -78 °C

18.2: 88 percent / PPh₃ / methanol / 0.17 h / 20 °C

19.1: tetrahydrofuran / 1 h / -78 °C

20.1: K₂CO₃ / methanol / 1 h

21.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

22.1: 0.29 g / NEt₃ / toluene

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; thionyl chloride; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 2.1: Jones oxidation / 14.1: Mitsunobu reaction / 22.1: 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,9R)-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 (913093-89-7)

Guidance literature:

Multi-step reaction with 23 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: DIAD; PPh₃ / tetrahydrofuran

16.1: K₂CO₃ / methanol

17.1: NEt₃ / CH₂Cl₂

18.1: 92 percent / imidazole / dimethylformamide

19.1: ozone / methanol / -78 °C

19.2: 88 percent / PPh₃ / methanol / 0.17 h / 20 °C

20.1: tetrahydrofuran / 1 h / -78 °C

21.1: K₂CO₃ / methanol / 1 h

22.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

23.1: 0.29 g / NEt₃ / toluene

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; n-butyllithium; thionyl chloride; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; bis(acetylacetonato) oxovanadium(IV); In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 3.1: Jones oxidation / 15.1: Mitsunobu reaction / 23.1: 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,9R)-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 (913093-89-7)

Guidance literature:

Multi-step reaction with 20 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: DIAD; PPh₃ / tetrahydrofuran

13.1: K₂CO₃ / methanol

14.1: NEt₃ / CH₂Cl₂

15.1: 92 percent / imidazole / dimethylformamide

16.1: ozone / methanol / -78 °C

16.2: 88 percent / PPh₃ / methanol / 0.17 h / 20 °C

17.1: tetrahydrofuran / 1 h / -78 °C

18.1: K₂CO₃ / methanol / 1 h

19.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

20.1: 0.29 g / NEt₃ / toluene

With pyridine; 1H-imidazole; aluminum oxide; sodium periodate; thionyl chloride; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; potassium tert-butylate; potassium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 12.1: Mitsunobu reaction / 20.1: 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,9R)-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

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

2-{4-[(2S,4S,5S,9R)-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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