(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

Base Information

Chemical Name:(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane
CAS No.:120093-57-4
Molecular Formula:C₂₇H₃₈O₂Si
Molecular Weight:422.683
Hs Code.:

Synonyms:(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

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Chemical Property of (2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

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Technology Process of (2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

There total 9 articles about (2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane 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: 90.0%

: 120093-53-0
[(S)-2-((R)-1,5-Dimethyl-hex-4-enyl)-oxiranyl]-methanol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 120093-57-4
(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

Guidance literature:: With 1H-imidazole;
DOI:10.1016/S0040-4039(00)86693-9

Reference yield:

: 2385-77-5
(R)-Citronellal

: 120093-57-4
(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

Guidance literature:: Multi-step reaction with 5 steps

1: 1) lithium diisopropylamide / 1) THF, -78 deg C, 45 min, 2a) THF, -78 deg C, 45 min, 2b) r.t., 5 h

2: 1) MeI, 2) 5 percent aq. NaHCO₃ / 1a) MeOH, 4 deg C, overnight, 1b) r.t., 5 h, 2) CH₂Cl₂, r.t., 16 h

3: 95 percent / CeCl₃*6H₂O, NaBH₄ / methanol / 0 °C / 5 to 10 min

4: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH₂Cl₂, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight

5: 90 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 5 h

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; cerium(III) chloride; (-)-diisopropyl tartrate; Cumene hydroperoxide; MS 3 Angstroem; sodium hydrogencarbonate; lithium diisopropyl amide; methyl iodide; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00034a017

Reference yield:

: 1117-61-9
(3R)-citronellol

: 120093-57-4
(2S)-2-<(1R)-1,5-Dimethyl-4-hexenyl>-2-<<(tert-butyldiphenylsilyl)oxy>methyl>oxirane

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / pyridinium chlorochromate, NaOAc / CH₂Cl₂ / 2 h

2: 1) lithium diisopropylamide / 1) THF, -78 deg C, 45 min, 2a) THF, -78 deg C, 45 min, 2b) r.t., 5 h

3: 1) MeI, 2) 5 percent aq. NaHCO₃ / 1a) MeOH, 4 deg C, overnight, 1b) r.t., 5 h, 2) CH₂Cl₂, r.t., 16 h

4: 95 percent / CeCl₃*6H₂O, NaBH₄ / methanol / 0 °C / 5 to 10 min

5: 1a) MS 3 Angstroem, diisopropyl (-)-tartrate, 1b) Ti(O-i-Pr)4, 2) cumene hydroperoxide / 1a) CH₂Cl₂, r.t., 1b) -5 deg C, 20 min, 2a) -5 deg C, 8 h, 2b) 4 deg C, overnight

6: 90 percent / imidazole, 4-(dimethylamino)pyridine / dimethylformamide / 5 h

With 1H-imidazole; titanium(IV) isopropylate; dmap; sodium tetrahydroborate; cerium(III) chloride; (-)-diisopropyl tartrate; Cumene hydroperoxide; MS 3 Angstroem; sodium acetate; sodium hydrogencarbonate; pyridinium chlorochromate; lithium diisopropyl amide; methyl iodide; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00034a017