2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane

Base Information

• Chemical Name: 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane
• CAS No.: 623151-53-1
• Molecular Formula: C₃₈H₅₈O₄Si₂
• Molecular Weight: 635.047

Synonyms:2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane

Chemical Property of 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane

There total 13 articles about 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane 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: 65.0%

2-[(1E,6Z,8E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undeca-1,6,8-trienyl]-[1,3]dioxane (623151-52-0) → 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane (623151-53-1)

Guidance literature:

With lithium perchlorate; In nitromethane; at 20 ℃;

DOI:10.1021/ol035900+

Reference yield:

4-(tert-butyldiphenylsilyloxy)-1-butyne (88158-68-3) → 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane (623151-53-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 0.42 h / 20 °C

1.2: 86 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 83 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / 3 h

3.1: 80 percent / MnO₂ / CH₂Cl₂ / 12 h

4.1: 4 Angstroem molecular sieves / toluene / 4 h / -78 °C

5.1: imidazole; DMAP / CH₂Cl₂; dimethylformamide / 12 h

6.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

6.2: 90 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 3 h / 0 °C

7.1: 79 percent / Zn; Cu(OAc)2*2H₂O; AgNO₃ / H₂O; methanol / 40 h

8.1: 99 percent / Dess-Martin periodinane; pyridine; water / CH₂Cl₂ / 1.67 h / 0 - 20 °C

9.1: NaH / tetrahydrofuran / 1.17 h / 0 - 20 °C

9.2: 87 percent / tetrahydrofuran / 1.17 h / 20 °C

10.1: 74 percent / DIBAL-H / tetrahydrofuran; hexane / 1.58 h / -78 °C

11.1: 83 percent / 2-methoxy-1,3-dioxane; TsOH*H₂O / tetrahydrofuran / 3 h

12.1: 65 percent / LiClO₄ / nitromethane / 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; 2-methoxy-1,3-dioxane; copper diacetate; 4 A molecular sieve; water; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; silver nitrate; triethylamine; zinc; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; nitromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2.1: Sonogashira coupling / 9.2: Horner-Wadsworth-Emmons olefination / 12.1: Diels-Alder reaction;

DOI:10.1021/ol035900+

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 2-{1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-inden-4-yl}-[1,3]dioxane (623151-53-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 99 percent / imidazole; DMAP / CH₂Cl₂; dimethylformamide

2.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 0.42 h / 20 °C

2.2: 86 percent / I₂ / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 83 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / 3 h

4.1: 80 percent / MnO₂ / CH₂Cl₂ / 12 h

5.1: 4 Angstroem molecular sieves / toluene / 4 h / -78 °C

6.1: imidazole; DMAP / CH₂Cl₂; dimethylformamide / 12 h

7.1: 9-BBN / tetrahydrofuran / 0 - 20 °C

7.2: 90 percent / H₂O₂; NaOH / tetrahydrofuran; H₂O / 3 h / 0 °C

8.1: 79 percent / Zn; Cu(OAc)2*2H₂O; AgNO₃ / H₂O; methanol / 40 h

9.1: 99 percent / Dess-Martin periodinane; pyridine; water / CH₂Cl₂ / 1.67 h / 0 - 20 °C

10.1: NaH / tetrahydrofuran / 1.17 h / 0 - 20 °C

10.2: 87 percent / tetrahydrofuran / 1.17 h / 20 °C

11.1: 74 percent / DIBAL-H / tetrahydrofuran; hexane / 1.58 h / -78 °C

12.1: 83 percent / 2-methoxy-1,3-dioxane; TsOH*H₂O / tetrahydrofuran / 3 h

13.1: 65 percent / LiClO₄ / nitromethane / 20 °C

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; copper(l) iodide; 9-borabicyclo[3.3.1]nonane dimer; Schwartz's reagent; 2-methoxy-1,3-dioxane; copper diacetate; 4 A molecular sieve; water; lithium perchlorate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; silver nitrate; triethylamine; zinc; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; nitromethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.1: Sonogashira coupling / 10.2: Horner-Wadsworth-Emmons olefination / 13.1: Diels-Alder reaction;

DOI:10.1021/ol035900+

upstream raw materials:

2-[(1E,6Z,8E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-4-methyl-undeca-1,6,8-trienyl]-[1,3]dioxane

4-(tert-butyldiphenylsilyloxy)-1-butyne

tert-butylchlorodiphenylsilane

(1E)-4-(tert-butyldiphenylsilanyloxy)-1-iodobut-1-ene

Downstream raw materials:

1-(tert-butyl-dimethyl-silanyloxy)-5-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2-methyl-2,3,3a,4,5,7a-hexahydro-1H-indene-4-carbaldehyde

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