(E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one

Base Information

• Chemical Name: (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one
• CAS No.: 122552-72-1
• Molecular Formula: C₃₂H₄₂O₃Si
• Molecular Weight: 502.769
• Mol file: 122552-72-1.mol

Synonyms:

Chemical Property of (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one

There total 21 articles about (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-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:

(R)-(+)-4-hydroxy-2-cyclopentenone (59995-47-0) → (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one (122552-72-1)

Guidance literature:

Multi-step reaction with 14 steps

1: AgNO₃ / pyridine

2: Br₂

3: Et₃N

6: 1)t-BuLi

7: HF

8: 1) ICl, 2)TBAF/HF

9: MeOH/p-TsOH

10: Swern oxidation

11: 56 percent / NiCl₂(1percent), CrCl₂ / dimethylsulfoxide; various solvent(s)

12: t-BuOOH, VO(acac)2

14: Bu₃SnH, AIBN

With chromium dichloride; methanol; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; silver nitrate; triethylamine; nickel dichloride; In pyridine; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)80638-3

Reference yield:

(1'R,2'R)-2-(2'-hydroxymethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid (98049-46-8) → (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one (122552-72-1)

Guidance literature:

Multi-step reaction with 16 steps

1: AgNO₃ / pyridine

2: 1) LiAlH₄, 2) Et(i-Pr)2N

3: 1) O₃, 2)NaBH₄

5: Bu₃SnH, AIBN

6: TBAF

7: Swern oxidation

8: 1)t-BuLi

9: HF

10: 1) ICl, 2)TBAF/HF

11: MeOH/p-TsOH

12: Swern oxidation

13: 56 percent / NiCl₂(1percent), CrCl₂ / dimethylsulfoxide; various solvent(s)

14: t-BuOOH, VO(acac)2

16: Bu₃SnH, AIBN

With chromium dichloride; methanol; tert.-butylhydroperoxide; sodium tetrahydroborate; lithium aluminium tetrahydride; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; ozone; silver nitrate; N-ethyl-N,N-diisopropylamine; nickel dichloride; In pyridine; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)80638-3

Reference yield:

(4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one (107657-42-1) → (E)-(3R,3aS,6aR,9aR)-3-(tert-Butyl-diphenyl-silanyloxy)-4-hydroxymethyl-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one (122552-72-1)

Guidance literature:

Multi-step reaction with 13 steps

1: Br₂

2: Et₃N

5: 1)t-BuLi

6: HF

7: 1) ICl, 2)TBAF/HF

8: MeOH/p-TsOH

9: Swern oxidation

10: 56 percent / NiCl₂(1percent), CrCl₂ / dimethylsulfoxide; various solvent(s)

11: t-BuOOH, VO(acac)2

13: Bu₃SnH, AIBN

With chromium dichloride; methanol; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; 2,2'-azobis(isobutyronitrile); hydrogen fluoride; tetrabutyl ammonium fluoride; bromine; tert.-butyl lithium; tri-n-butyl-tin hydride; Iodine monochloride; toluene-4-sulfonic acid; triethylamine; nickel dichloride; In dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)80638-3

upstream raw materials:

C₃₆H₄₂N₂O₄SSi

(R)-(+)-4-hydroxy-2-cyclopentenone

(1'R,2'R)-2-(2'-hydroxymethyl-2'-methyl-3'-methylenecyclopentyl)ethanoic acid

(4R)-(+)-4-[(1,1-dimethylethyl)diphenylsilyloxy]cyclopent-2-en-1-one

Downstream raw materials:

(E)-(1R,3R,3aS,6aR,9aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-1,9a-dimethyl-1,2,3,3a,6,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-1-ol

(E)-(3R,3aS,6aR,9aR)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-(tert-butyl-diphenyl-silanyloxy)-9a-methyl-3,3a,6,6a,7,8,9,9a,10,10a-decahydro-2H-dicyclopenta[a,d]cycloocten-1-one