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

Base Information

• Chemical Name: 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
• CAS No.: 913093-90-0
• Molecular Formula: C₃₁H₄₆O₅Si
• Molecular Weight: 526.789

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 24 articles about 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 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: 89.0%

(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) → 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 (913093-90-0)

Guidance literature:

With lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1002/ejoc.200600284

Reference yield:

(1R,3R,5R)-5-isopropenyl-2,2-dimethyl-1-vinylcyclohexane-1,3-diol (913093-74-0) → 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 (913093-90-0)

Guidance literature:

Multi-step reaction with 23 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

23.1: 89 percent / lithium tris[(3-ethyl-3-pentyl)oxy]hydridoaluminate / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; thionyl chloride; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; 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) → 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 (913093-90-0)

Guidance literature:

Multi-step reaction with 24 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

24.1: 89 percent / lithium tris[(3-ethyl-3-pentyl)oxy]hydridoaluminate / tetrahydrofuran / 0.5 h / -78 °C

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; n-butyllithium; thionyl chloride; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; 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

upstream raw materials:

(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

(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:

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

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

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