3,8-Dioxabicyclo[3.2.1]octan-1-ol, 4-[5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methylpentyl]-4-methyl-, (1S,4S,5R)-

Base Information

• Chemical Name: 3,8-Dioxabicyclo[3.2.1]octan-1-ol, 4-[5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methylpentyl]-4-methyl-, (1S,4S,5R)-
• CAS No.: 849411-91-2
• Molecular Formula: C₂₉H₄₂O₄Si
• Molecular Weight: 482.736
• Mol file: 849411-91-2.mol

Synonyms:

Chemical Property of 3,8-Dioxabicyclo[3.2.1]octan-1-ol, 4-[5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methylpentyl]-4-methyl-, (1S,4S,5R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,8-Dioxabicyclo[3.2.1]octan-1-ol, 4-[5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methylpentyl]-4-methyl-, (1S,4S,5R)-

There total 12 articles about 3,8-Dioxabicyclo[3.2.1]octan-1-ol, 4-[5-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-4-methylpentyl]-4-methyl-, (1S,4S,5R)- 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:

(+-)-2-methyl-pent-4-enoic acid (1575-74-2) → (4S,5R)-4-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-4-methyl-3,8-dioxabicyclo[3.2.1]octan-1-ol (849411-91-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: LiAlH₄ / tetrahydrofuran / 16 h / 20 °C

2.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

3.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

3.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

4.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

5.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

6.1: LiAlH₄ / diethyl ether / 0 - 20 °C

7.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

8.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

9.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

11.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

12.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

13.1: 97 percent / H₂ / Pd/C / ethanol / 16 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 3.2: Suzuki-Miyaura coupling / 4.1: Sharpless dihydroxylation / 12.1: Horner-Wadsworth-Emmons cyclization;

DOI:10.1021/jo048115z

Reference yield:

2-methylpent-4-en-1-ol (5673-98-3) → (4S,5R)-4-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-4-methyl-3,8-dioxabicyclo[3.2.1]octan-1-ol (849411-91-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 91 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

2.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

3.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

4.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

5.1: LiAlH₄ / diethyl ether / 0 - 20 °C

6.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

8.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

9.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

10.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

11.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

12.1: 97 percent / H₂ / Pd/C / ethanol / 16 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.2: Suzuki-Miyaura coupling / 3.1: Sharpless dihydroxylation / 11.1: Horner-Wadsworth-Emmons cyclization;

DOI:10.1021/jo048115z

Reference yield:

tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane (144693-95-8) → (4S,5R)-4-[5-(tert-butyldiphenylsilanyloxy)-4-methylpentyl]-4-methyl-3,8-dioxabicyclo[3.2.1]octan-1-ol (849411-91-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 9-BBN dimer / tetrahydrofuran / 2 h / 0 °C

1.2: 74 percent / K₃PO₄ / Pd(PPh₃)4 / tetrahydrofuran; dioxane / 5 h / 85 °C

2.1: AD-mix-β; MeSO2NH2 / H2O; 2-methyl-propan-2-ol; toluene / 30 h / 0 °C

3.1: 74 percent / n-Bu₄NI; Ag₂O / CH₂Cl₂ / 5 h / 20 °C

4.1: LiAlH₄ / diethyl ether / 0 - 20 °C

5.1: 0.445 g / NaH / tetrahydrofuran / 3 h / 0 - 20 °C

6.1: [Rh(OAc)2]2 / toluene / 2 h / 110 °C

7.1: 118 mg / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

8.1: 84 percent / Me₃SiBr / CH₂Cl₂ / 0.5 h / -40 °C

9.1: pyridinium dichromate / CH₂Cl₂ / 2 h / 20 °C

10.1: 29 mg / NaH / tetrahydrofuran / 1.25 h / 0 - 20 °C

11.1: 97 percent / H₂ / Pd/C / ethanol / 16 h / 20 °C

With lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; trimethylsilyl bromide; methanesulfonamide; AD-mix-β; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; silver(l) oxide; dimeric 9-borabicyclo[3.3.1]nonane; dirhodium tetraacetate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; toluene; tert-butyl alcohol; 1.2: Suzuki-Miyaura coupling / 2.1: Sharpless dihydroxylation / 10.1: Horner-Wadsworth-Emmons cyclization;

DOI:10.1021/jo048115z

upstream raw materials:

(+-)-2-methyl-pent-4-enoic acid

2-methylpent-4-en-1-ol

tert-butyldipheny((2-methylpent-4-en-1-yl)oxy)silane

(Z)-ethyl 8-(tert-butyldiphenylsilanyloxy)-3,7-dimethyloct-2-enoate