tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

Base Information

Chemical Name:tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether
CAS No.:642072-03-5
Molecular Formula:C₃₃H₅₂OSi
Molecular Weight:492.861
Hs Code.:

Synonyms:tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

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Chemical Property of tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

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Technology Process of tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

There total 5 articles about tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether 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: 61.0%

: 60106-53-8
n-hexyltriphenylphosphonium iodide

: 642072-02-4
(7S)-10-{[tert-butyl(diphenyl)silyl]oxy}-7-methyldecanal

: 642072-03-5
tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

Guidance literature:: n-hexyltriphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; hexane; at 0 ℃; for 2h;

(7S)-10-{[tert-butyl(diphenyl)silyl]oxy}-7-methyldecanal; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h;
DOI:10.1016/j.tet.2003.09.085

Reference yield:

: (6S,6aR,7R,9aR)-6-Bromo-7-methyl-octahydro-cyclopenta[b]oxocin-2-one

: 642072-03-5
tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1.25 g / TsOH*H₂O / CH₂Cl₂ / 24 h

2.1: 77 percent / NaOEt; NaBH₄ / ethanol / 2 h / 20 °C

3.1: 83 percent / H₂ / Pd/C / ethyl acetate / 1 h / 3040 Torr

4.1: 81 percent / imidazole; DMAP / dimethylformamide / 4 h / 20 °C

5.1: 89 percent / DIBAL-H / toluene / 1 h / -78 °C

6.1: nBuLi / tetrahydrofuran; hexane / 2 h / 0 °C

6.2: 61 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; n-butyllithium; hydrogen; sodium ethanolate; diisobutylaluminium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 2.1: Grob fragmentation / 6.2: Wittig reaction;
DOI:10.1016/j.tet.2003.09.085

Reference yield:

: 642071-92-9
ethyl (5Z,7R)-10-hydroxy-7-methyl-5-decenoate

: 642072-03-5
tert-butyl(diphenyl)silyl (4S)-4-methyl-10-hexadecenyl ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: 83 percent / H₂ / Pd/C / ethyl acetate / 1 h / 3040 Torr

2.1: 81 percent / imidazole; DMAP / dimethylformamide / 4 h / 20 °C

3.1: 89 percent / DIBAL-H / toluene / 1 h / -78 °C

4.1: nBuLi / tetrahydrofuran; hexane / 2 h / 0 °C

4.2: 61 percent / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

With 1H-imidazole; dmap; n-butyllithium; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; toluene; 4.2: Wittig reaction;
DOI:10.1016/j.tet.2003.09.085