<2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

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Chemical Name:<2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane
CAS No.:152033-16-4
Molecular Formula:C₃₈H₅₈O₃Si
Molecular Weight:590.962
Hs Code.:

Synonyms:<2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

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Chemical Property of <2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

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Technology Process of <2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

There total 36 articles about <2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane 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: 79.0%

: <2(3S,4S,5R),5R,6S,6(3S)>-2-Hydroxy-2-<4-(methoxymethoxy)-3,5-dimethyl-8-<<(1,1-dimethylethyl)diphenylsilyl>oxy>octyl>-5-methyl-6-(3-methyl-4-pentenyl)tetrahydropyran

: 152033-16-4
<2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

Guidance literature:: With trimethylsilyl bromide; In dichloromethane; 1.) -30 deg C, 5 min, 2.) 3 deg C, 30 min;
DOI:10.1021/jo00121a026

Reference yield:

: Ethyl (4R)-5-(tetrahydropyran-2-yloxy)-4-methyl-2-pentenoate

: 152033-16-4
<2S,2(1R),3S,6R,8S,8(3S),9R>-3,9-Dimethyl-2-<1-methyl-4-<<(1,1-dimethylethyl)diphenylsilyl>oxy>butyl>-8-(3-methyl-4-pentenyl)-1,7-dioxaspiro<5.5>undecane

Guidance literature:: Multi-step reaction with 15 steps

1: H₂ / 10percent Pd/C / ethyl acetate / 6 h / 25 °C

2: LiAlH₄ / diethyl ether / 0.5 h / 25 °C

3: 99 percent / imidazole / dimethylformamide / 18 h / 25 °C

4: 80 percent / p-TsOH*H₂O / methanol / 0.83 h / 25 °C

5: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 25 deg C, 30 min

6: BF₃*Et₂O / CH₂Cl₂ / 1.) -86 deg C, 15 min; -86 to -70 deg C, 45 min, 2.) 0 deg C, 1 h

7: 100 percent / i-Pr₂NEt / CH₂Cl₂ / 18 h / 25 °C

8: 1.) 9-BBN, 2.) 3 N aq. NaOH, 31percent aq. H₂O₂ / 1.) THF, 25 deg C, 17 h, 2.) 25 deg C, 7 h

9: 87 percent / pyridine, n-Bu₃P / 45 h / 25 °C

10: 100 percent / 80percent m-CPBA, NaHCO₃ / CH₂Cl₂ / 1.5 h / 25 °C

11: n-BuLi / diethyl ether; hexane / 1.) -78 deg C, 30 min, 2.) 25 deg C, 4.5 h

12: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) 5 deg C, 30 min

13: 51 percent / SmI₂ / tetrahydrofuran; methanol / 0.33 h / -78 °C

14: 91 percent / K₂CO₃ / methanol / 2.5 h / 60 °C

15: 79 percent / TMSBr / CH₂Cl₂ / 1.) -30 deg C, 5 min, 2.) 3 deg C, 30 min

With pyridine; 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; samarium diiodide; oxalyl dichloride; trimethylsilyl bromide; tributylphosphine; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00121a026