(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

Base Information

Chemical Name:(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol
CAS No.:189164-15-6
Molecular Formula:C₂₉H₄₄O₃Si
Molecular Weight:468.752
Hs Code.:

Synonyms:(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

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Chemical Property of (E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

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Technology Process of (E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

There total 18 articles about (E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol 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:

: 1026040-95-8
tert-Butyl-((E)-(1R,9S)-9-methoxy-1-methyl-11-trityloxy-undec-5-enyloxy)-diphenyl-silane

: 189164-15-6
(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃; for 6h; Yield given;
DOI:10.1021/jo962217a

Reference yield:

: 56718-04-8
(4R)-pentane-1,4-diol

: 189164-15-6
(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1: 83 percent / DMAP, Et₃N / CH₂Cl₂ / 24 h

2: 96 percent / imidazole / dimethylformamide / 17 h

3: 88 percent / PPTS / ethanol / 6 h / 55 °C

4: 77 percent / DMAP / CH₂Cl₂ / Ambient temperature

5: 86 percent / dimethylsulfoxide / 1 h / Ambient temperature

6: 1.) n-BuLi / 1.) THF, room temperature, 1 h, 2.) HMPT, room temperature, 16 h.

7: TBAF / tetrahydrofuran / 16 h / Ambient temperature

8: LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

9: DMAP, Et₃N / CH₂Cl₂ / 24 h

10: imidazole / dimethylformamide / 17 h

11: PPTS / ethanol / 6 h / 55 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; triethylamine; In tetrahydrofuran; ethanol; dichloromethane; diethylene glycol dimethyl ether; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo962217a

Reference yield:

: 4328-94-3
pentane-1,3,5-triol

: 189164-15-6
(E)-(3S,11R)-11-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-dodec-6-en-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1: 1.) TsOH, HC(OMe)3, 2.) 1N NaOH / 1.) CH₂Cl₂, room temperature, overnight, 2.) MeOH, room temperature, 12 h.

2: DMAP / CH₂Cl₂

3: SiO₂, 6N HCl / CH₂Cl₂ / Ambient temperature

4: DIEA, DMAP / CH₂Cl₂ / 24 h / Ambient temperature

5: NaH / dimethylformamide / 1.) -5 deg C, 1 h, 2.) to room temperatire, 3 h.

6: NaI / acetone / 16 h / Heating

7: 1.) n-BuLi / 1.) THF, room temperature, 1 h, 2.) HMPT, room temperature, 16 h.

8: TBAF / tetrahydrofuran / 16 h / Ambient temperature

9: LiAlH₄ / bis-(2-methoxy-ethyl) ether / 24 h / Heating

10: DMAP, Et₃N / CH₂Cl₂ / 24 h

11: imidazole / dimethylformamide / 17 h

12: PPTS / ethanol / 6 h / 55 °C

With 1H-imidazole; hydrogenchloride; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; silica gel; sodium hydride; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; trimethyl orthoformate; In tetrahydrofuran; ethanol; dichloromethane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo962217a