(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

Base Information

Chemical Name:(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone
CAS No.:166523-53-1
Molecular Formula:C₂₂H₃₃BrO₃Si
Molecular Weight:453.492
Hs Code.:

Synonyms:(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

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Chemical Property of (5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

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Technology Process of (5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

There total 9 articles about (5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone 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:

: (2S,3R)-2-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-6-phenylselanyl-cyclohexanone

: 166523-53-1
(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

Guidance literature:: With dihydrogen peroxide; In dichloromethane; at 35 ℃;
DOI:10.1021/jm950747d

Reference yield:

: 63272-66-2
4-bromo-2-hydroxy-5-methoxybenzaldehyde

: 166523-53-1
(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 7 steps

1: imidazole, DMAP / CH₂Cl₂ / Ambient temperature

2: NaBH₄ / methanol / 0 °C

3: Ph₃P, Br₂ / dimethylformamide / 0 °C

4: 1.) LDA, HMPA / 1.) THF, -35 deg C, 2.) THF, -35 deg C

5: CaCO₃ / CCl₄ / 65 °C

6: 1.) CuI / 1.) ET₂O, 0 deg C, 2.) Et₂O, 0 deg C

7: aq. H₂O₂ / CH₂Cl₂ / 35 °C

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium tetrahydroborate; copper(l) iodide; dihydrogen peroxide; bromine; triphenylphosphine; calcium carbonate; lithium diisopropyl amide; In methanol; tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jm950747d

Reference yield:

: 88154-77-2
(5R)-5-methyl-2-(phenylsulfinyl)cyclohexan-1-one

: 166523-53-1
(5R,6S)-6-[4-Bromo-2-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-benzyl]-3,5-dimethyl-cyclohex-2-enone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA, HMPA / 1.) THF, -35 deg C, 2.) THF, -35 deg C

2: CaCO₃ / CCl₄ / 65 °C

3: 1.) CuI / 1.) ET₂O, 0 deg C, 2.) Et₂O, 0 deg C

4: aq. H₂O₂ / CH₂Cl₂ / 35 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; dihydrogen peroxide; calcium carbonate; lithium diisopropyl amide; In tetrachloromethane; dichloromethane;
DOI:10.1021/jm950747d