(2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

Base Information

Chemical Name:(2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane
CAS No.:104996-38-5
Molecular Formula:C₂₉H₄₀O₃Si
Molecular Weight:464.72
Hs Code.:

Synonyms:(2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

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Chemical Property of (2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

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Technology Process of (2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

There total 16 articles about (2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-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: 97.0%

: 112320-67-9,112419-63-3
2(S)-vinyl-4(S)-hydroxy-8(R),9(S)-dimethyl-1,7-dioxaspiro<5.5>undecane

: 58479-61-1
tert-butylchlorodiphenylsilane

: 104996-38-5,112419-64-4
2(S)-vinyl-4(S)-<(tert-butyldiphenylsilyl)oxy>-8(R),9(S)-dimethyl-1,7-dioxaspiro<5.5>undecane

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; for 48h;
DOI:10.1021/jo00238a031

Reference yield:

: 104705-88-6
(6S,8R,9S)-methyl 8,9-dimethyl-4-oxo-1,7-dioxaspiro<5,5>undec-2-ene-2-carboxylate

: 104996-38-5
(2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / Rh-Al₂O₃ / ethanol

2: 1.) imidazole, 2.) LiN(i-Pr)2 then HOAc / 1.) DMF, 2.) THF, -78 deg C

3: 1.) i-Bu₂AlH / 1.) toluene, -78 deg C, 2.) THF, 0 deg C

With 1H-imidazole; hydrogen; diisobutylaluminium hydride; acetic acid; lithium diisopropyl amide; rhodium on alumina; In ethanol;
DOI:10.1039/c39860000479

Reference yield:

: 104996-32-9
1,1,1-trimethoxy-2,4-pentanedione

: 104996-38-5
(2S,4R,6S,8R,9S)-4-<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-2-ethenyl-1,7-dioxaspiro<5.5>undecane

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

2: TsOH*H₂O / CH₂Cl₂ / 0.5 h

3: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

4: 96 percent / imidazole / dimethylformamide / 1 h / 0 - 20 °C

5: 91 percent / LDA / tetrahydrofuran / 1 h / -78 °C

6: 89 percent / (i-Bu)2AlH / toluene / 2.5 h / -78 °C

7: 1.) n-BuLi / 1.) THF, 0 deg C, 2 h, 2.) THF, from -78 deg C to 0 deg C, 20 min

With 1H-imidazole; n-butyllithium; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; rhodium on aluminium; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo00375a017