[(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane

Base Information

• Chemical Name: [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane
• CAS No.: 114066-23-8
• Molecular Formula: C₃₄H₄₉BrO₃Si
• Molecular Weight: 613.751
• Mol file: 114066-23-8.mol

Synonyms:[(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane

Chemical Property of [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane

There total 17 articles about [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane 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: 93.0%

2(R)-(3-methyl-4-hydroxy-2(E)-butenyl)-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane (114066-22-7) → [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane (114066-23-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In acetonitrile; for 1h;

DOI:10.1016/S0040-4039(00)96346-9

Reference yield:

Acetic acid (2S,3R)-2,4-dimethyl-3-(tetrahydro-pyran-2-yloxy)-pentyl ester → [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane (114066-23-8)

Guidance literature:

Multi-step reaction with 17 steps

1: K₂CO₃ / methanol / 2 h / 25 °C

2: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂

3: 89 percent / benzene / 24 h / 80 °C

4: PPTS / methanol / 5 h

5: H₂ / Pd/C / ethanol

6: PPTS / CH₂Cl₂ / 0.75 h / 40 °C

7: tetrahydrofuran / 1 h / -78 °C

8: K₂CO₃ / 18 h

9: 30percent HClO₄ / CH₂Cl₂ / 0.33 h / ultrasound was used

10: 78 percent / copper

11: NaBH₄ / methanol / 0.5 h

12: DMAP, imidazole / dimethylformamide / 48 h

13: 1.) 9-BBN, THF, ultrasound, 1h 2.) H₂O₂

14: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

15: 89 percent / benzene / 1 h / 80 °C / Heating

16: 91 percent / diisobutylaluminium hydride / tetrahydrofuran / 3 h / -78 °C

17: 93 percent / carbon tetrabromide, triphenyl phosphine / acetonitrile / 1 h

With 1H-imidazole; dmap; sodium tetrahydroborate; perchloric acid; oxalyl dichloride; carbon tetrabromide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; palladium on activated charcoal; copper; In tetrahydrofuran; methanol; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)96346-9

Reference yield:

4-methylpent-2-en-1-ol (5362-55-0) → [(2R,4S,6R,8R,9S)-2-((E)-4-Bromo-3-methyl-but-2-enyl)-8-isopropyl-9-methyl-1,7-dioxa-spiro[5.5]undec-4-yloxy]-tert-butyl-diphenyl-silane (114066-23-8)

Guidance literature:

Multi-step reaction with 20 steps

1: 1.) asymmetric epoxidation

2: pyridine / diethyl ether / 1 h / 0 °C

3: PPTS / CH₂Cl₂ / 3 h

4: K₂CO₃ / methanol / 2 h / 25 °C

5: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂

6: 89 percent / benzene / 24 h / 80 °C

7: PPTS / methanol / 5 h

8: H₂ / Pd/C / ethanol

9: PPTS / CH₂Cl₂ / 0.75 h / 40 °C

10: tetrahydrofuran / 1 h / -78 °C

11: K₂CO₃ / 18 h

12: 30percent HClO₄ / CH₂Cl₂ / 0.33 h / ultrasound was used

13: 78 percent / copper

14: NaBH₄ / methanol / 0.5 h

15: DMAP, imidazole / dimethylformamide / 48 h

16: 1.) 9-BBN, THF, ultrasound, 1h 2.) H₂O₂

17: (COCl)2, Et₃N / dimethylsulfoxide; CH₂Cl₂ / -78 °C

18: 89 percent / benzene / 1 h / 80 °C / Heating

19: 91 percent / diisobutylaluminium hydride / tetrahydrofuran / 3 h / -78 °C

20: 93 percent / carbon tetrabromide, triphenyl phosphine / acetonitrile / 1 h

With pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; perchloric acid; oxalyl dichloride; carbon tetrabromide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; triethylamine; triphenylphosphine; palladium on activated charcoal; copper; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)96346-9

upstream raw materials:

2(R)-(3-methyl-4-hydroxy-2(E)-butenyl)-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane

4-methylpent-2-en-1-ol

1-hydroxy-1(R)-isopropyl-9-methoxy-2(S)-methylnon-8-en-6-yn-5-one

1-hydroxy-1(R)-isopropyl-7,9,9-trimethoxy-2(S)-methylnon-6-en-5-one

Downstream raw materials:

2(R)-<3,5(R)-dimethyl-6-hydroxy-2(E)-hexenyl>-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R)-isopropyl-9(S)-methyl-1,7-dioxaspiro<5.5>undecane