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

Base Information

• Chemical Name: 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
• CAS No.: 913093-92-2
• Molecular Formula: C₃₆H₅₃ClO₈Si
• Molecular Weight: 677.351

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 26 articles about 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 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) → 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 (913093-92-2)

Guidance literature:

Multi-step reaction with 25 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

24.1: 86 percent / Cs₂CO₃ / acetonitrile

25.1: 62 mg / 1-chloro-N,N,2-trimethyl-1-propenylamine / CH₂Cl₂ / 0.75 h

With pyridine; 1H-imidazole; chromium(VI) oxide; tert.-butylhydroperoxide; aluminum oxide; sodium periodate; thionyl chloride; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; caesium 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 / 24.1: Michael addition;

DOI:10.1002/ejoc.200600284

Reference yield:

2,2-dimethyl-3(R)-hydroxy-5(R)-isopropylenecyclohexanone (97643-04-4) → 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 (913093-92-2)

Guidance literature:

Multi-step reaction with 26 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

25.1: 86 percent / Cs₂CO₃ / acetonitrile

26.1: 62 mg / 1-chloro-N,N,2-trimethyl-1-propenylamine / CH₂Cl₂ / 0.75 h

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; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; caesium 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 / 25.1: Michael addition;

DOI:10.1002/ejoc.200600284

Reference yield:

(1S,3R,5R)-5-Isopropenyl-2,2-dimethyl-1-(R)-oxiranyl-cyclohexane-1,3-diol → 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 (913093-92-2)

Guidance literature:

Multi-step reaction with 24 steps

1.1: 9.5 g / CrO₃; aq. H₂SO₄ / acetone / 0.33 h / 0 °C

2.1: 91 percent / K₂CO₃ / acetonitrile / 2 h

3.1: 92 percent / naphthalenesulfonic acid / CH₂Cl₂ / 2 h

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

4.2: 97 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 94 percent / NaIO₄ / methanol; H₂O

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

6.2: K₂CO₃ / tetrahydrofuran; H₂O

7.1: 5.54 g / LiAl(t-BuO)3H / tetrahydrofuran / 0.33 h / 0 °C

8.1: ozone / methanol / -78 °C

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

8.3: 77 percent / FeSO₄*7H₂O / methanol / 1.67 h / 0 °C

9.1: tetrahydrofuran / 1 h / 0 °C

10.1: 4.27 g / NEt₃ / CH₂Cl₂ / 2 h / 0 °C

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

12.1: Al₂O₃ / H₂O

13.1: DIAD; PPh₃ / tetrahydrofuran

14.1: K₂CO₃ / methanol

15.1: NEt₃ / CH₂Cl₂

16.1: 92 percent / imidazole / dimethylformamide

17.1: ozone / methanol / -78 °C

17.2: 88 percent / PPh₃ / methanol / 0.17 h / 20 °C

18.1: tetrahydrofuran / 1 h / -78 °C

19.1: K₂CO₃ / methanol / 1 h

20.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

21.1: 0.29 g / NEt₃ / toluene

22.1: 89 percent / lithium tris[(3-ethyl-3-pentyl)oxy]hydridoaluminate / tetrahydrofuran / 0.5 h / -78 °C

23.1: 86 percent / Cs₂CO₃ / acetonitrile

24.1: 62 mg / 1-chloro-N,N,2-trimethyl-1-propenylamine / CH₂Cl₂ / 0.75 h

With pyridine; 1H-imidazole; chromium(VI) oxide; aluminum oxide; sodium periodate; thionyl chloride; lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride; 1-chloro-1-(dimethylamino)-2-methyl-1-propene; di-isopropyl azodicarboxylate; naphthalenesulfonic acid; sulfuric acid; potassium tert-butylate; potassium carbonate; caesium carbonate; Dess-Martin periodane; ozone; lithium tri-t-butoxyaluminum hydride; triethylamine; triphenylphosphine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; 1.1: Jones oxidation / 13.1: Mitsunobu reaction / 21.1: Wittig reaction / 23.1: Michael addition;

DOI:10.1002/ejoc.200600284

upstream 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

(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

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 913093-92-2 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

Send

Send

Metric Ton KG G Pound L ML

Send

Send