tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

Base Information

Chemical Name:tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane
CAS No.:287483-50-5
Molecular Formula:C₂₇H₃₈O₃Si
Molecular Weight:438.682
Hs Code.:

Synonyms:tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

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Chemical Property of tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

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Technology Process of tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

There total 18 articles about tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane 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: 100.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 369375-79-1
(2S,3S,5S)-5-(S)-Oxiranyl-2-pentyl-tetrahydro-furan-3-ol

: 287483-50-5
tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

Guidance literature:: With 1H-imidazole; In dichloromethane;
DOI:10.1016/S0957-4166(01)00244-0

Reference yield: 80.0%

: 287483-49-2
(2R)-2-[(4S,5S,2S)-4-(tert-butyldiphenylsilanyloxy)-5-pentyltetrahydrofuran-2-yl]-2-methanesulfonyloxy-ethyl benzoate

: 287483-50-5
tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

Guidance literature:: With sodium hydride; In methanol; dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4039(00)00595-5

Reference yield:

: 28163-88-4,4124-88-3
(E)-non-3-enoic acid

: 287483-50-5
tert-butyl-[5-((2S)-oxiran-2-yl)-2-(2S,3S,5S)-2-pentyltetrahydrofuran-3-yloxy]-diphenylsilane

Guidance literature:: Multi-step reaction with 10 steps

1: 77 g / Me₃SiCl / 2 h / 20 °C

2: 82 percent / AD-mix-α; MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 20 h / 0 °C

3: 96 percent / imidazole / CH₂Cl₂ / 0 - 20 °C

4: DIBAL-H / diethyl ether; cyclohexane / -78 °C

5: 18.5 g / benzene / 2 h / 50 °C

6: 77 percent / DIBAL-H / diethyl ether; cyclohexane / 0 °C

7: 82 percent / Ti(OPr-i)4; (S,S)-(-)-DET; TBHP / 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 2 h / -20 °C

8: Et₃N / CH₂Cl₂ / 2 h / 0 °C

9: 1.56 g / Et₃N / CH₂Cl₂ / 1 h / 0 °C

10: 80 percent / NaH; MeOH / CH₂Cl₂ / 0 - 20 °C

With 1H-imidazole; titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; AD-mix-α; chloro-trimethyl-silane; diethyl (2S,3S)-tartrate; methanesulfonamide; sodium hydride; diisobutylaluminium hydride; triethylamine; 4 A molecular sieve; In 2,2,4-trimethylpentane; diethyl ether; dichloromethane; cyclohexane; water; tert-butyl alcohol; benzene; 5: Wittig olefination / 7: Katsuki-Sharpless asymmetric epoxidation;
DOI:10.1021/jo0057194