(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

Base Information

Chemical Name:(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene
CAS No.:131413-95-1
Molecular Formula:C₂₄H₃₁BrOSi
Molecular Weight:443.499
Hs Code.:

Synonyms:(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

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Chemical Property of (1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

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Technology Process of (1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

There total 1 articles about (1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene 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: 92.0%

: 135419-79-3
(1E,3S,4S)-1-bromo-2,4-dimethylhexa-1,5-dien-3-ol

: 58479-61-1
tert-butylchlorodiphenylsilane

: 131413-95-1
(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

Guidance literature:: With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 50 ℃; for 96h;

Reference yield:

: 131413-95-1
(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

: 65195-55-3
avermectin B₁a

Guidance literature:: Multi-step reaction with 23 steps

2: 94 percent / 4-dimethylaminopyridine, NEt₃ / dimethylformamide / 15 h / Ambient temperature

3: 1.) BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 2 min, 2.) -78 deg C, 2 h, then -78 deg C -> RT, 12 h

5: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine, 2.) NEt₃ / 1.) CHCl₃, 10 min, 2.) 50 deg C, 3 h

6: 98 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.08 h / Heating

7: 95 percent / imidazole / dimethylformamide / 16 h / Ambient temperature

8: 77 percent / OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 100 h / Ambient temperature

9: 86 percent / NaIO₄, KH₂PO₄ / methanol; H₂O / 3 h / Ambient temperature

10: 1.) tert-BuLi / 1.) pentane, THF, -78 deg C, 10 min, 2.) -78 deg C, 1 h

11: 34 percent / 6percent Na/Hg, Na₂HPO₄ / tetrahydrofuran; methanol / 2 h / -40 °C

12: 93 percent / tetrabutylammonium fluoride / tetrahydrofuran / 36 h / Heating

13: tris(triphenylphosphine)ruthenium(II) chloride / benzene; CH₂Cl₂ / 48 h / Ambient temperature

14: 32 percent / NaClO₂, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H₂O / 1 h / Ambient temperature

15: 47 percent / 2-chloro-1-methylpyridinium iodide, NEt₃ / acetonitrile / 4 h / Heating

16: 61 percent / N-methylmorpholine N-oxide, tetrapropylammonium perruthenate / CH₂Cl₂ / 1 h / Ambient temperature

17: 88 percent / NEt₃ / CH₂Cl₂ / 4 h / 0 °C

18: 44 percent / CH₂Cl₂ / 2 h / -78 °C

19: 87 percent / 40percent aq. HF, pyridine / acetonitrile / 36 h / Ambient temperature

20: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine, 2.) NaBH₄, CeCl₃ / 1.) CHCl₃, RT, 30 min, 2.) MeOH, 0 deg C, 15 min

21: 97 percent / pyridine, 4-dimethylaminopyridine (DMAP) / 1.5 h / Ambient temperature

22: 64 percent / AgClO₄, CaCO₃ / toluene / 0.17 h / Ambient temperature

23: 90 percent / LiBHEt₃ / tetrahydrofuran / -78 °C

With pyridine; 1H-imidazole; dmap; sodium chlorite; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; cerium(III) chloride; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; tris(triphenylphosphine)ruthenium(II) chloride; 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine; boron trifluoride diethyl etherate; hydrogen fluoride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; tert.-butyl lithium; silver perchlorate; lithium triethylborohydride; 4-methylmorpholine N-oxide; triethylamine; calcium carbonate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; benzene;

Reference yield:

: 131413-95-1
(1E,3S,4S)-1-bromo-3-(tert-butyldiphenylsilyloxy)-2,4-dimethylhexa-1,5-diene

: 135419-80-6
<2R(2E,4S,5S),4S,6S,8R(S),9S>-2-<4-(tert-butyldiphenylsilyloxy)-3,5-dimethylhepta-2,6-dienyl>-9-methyl-8-(1-methypropyl)-1,7-dioxaspiro<5.5>undec-10-en-4-ol

Guidance literature:: Multi-step reaction with 5 steps

2: 94 percent / 4-dimethylaminopyridine, NEt₃ / dimethylformamide / 15 h / Ambient temperature

3: 1.) BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 2 min, 2.) -78 deg C, 2 h, then -78 deg C -> RT, 12 h

5: 1.) 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine, 2.) NEt₃ / 1.) CHCl₃, 10 min, 2.) 50 deg C, 3 h

With dmap; n-butyllithium; 2-(phenylsulphonyl)-3-(p-nitrophenylsulphonyl)oxaziridine; boron trifluoride diethyl etherate; triethylamine; In N,N-dimethyl-formamide;