(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

Base Information

Chemical Name:(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol
CAS No.:853996-01-7
Molecular Formula:C₂₈H₄₇BrO₅Si
Molecular Weight:571.668
Hs Code.:

(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

Synonyms:(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

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Chemical Property of (2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

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Technology Process of (2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

There total 16 articles about (2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-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: 81.0%

: 853996-00-6
(2R,3S,5S,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-one

: (2R,3R,4R,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

: 853996-01-7
(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

Guidance literature:: With sodium tetrahydroborate; In ethanol; at -78 ℃; for 2.5h;
DOI:10.1021/ja051420x DOI:10.1021/ja060369+

Reference yield:

: 853995-97-8
2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde

: 853996-01-7
(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 94 percent / diisopropylethylamine / dimethylformamide / 1.5 h / 20 °C

2.1: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

3.1: 85 percent / tetrahydrofuran / 24 h / Heating

4.1: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

5.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C

5.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C

6.1: 81 percent / NaBH₄ / ethanol / 2.5 h / -78 °C

With sodium tetrahydroborate; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; 2.1: Kurihara condensation / 3.1: Petasis-Tebbe reaction / 4.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ja060369+

Reference yield:

: 853995-98-9
(S)-4-Benzyl-3-((2S,3R,6S)-3-hydroxy-2,6-dimethyl-oct-7-enoyl)-oxazolidin-2-one

: 853996-01-7
(2R,3R,4S,5R,6R)-2-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 1 h / 0 °C

2.1: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

3.1: 85 percent / tetrahydrofuran / 24 h / Heating

4.1: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

5.1: LHMDS / tetrahydrofuran; hexane / 1.5 h / -78 - -10 °C

5.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C

6.1: 81 percent / NaBH₄ / ethanol / 2.5 h / -78 °C

With lithium hydroxide; sodium tetrahydroborate; isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dihydrogen peroxide; dimethylaluminum chloride; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; hexane; dichloromethane; 2.1: Kurihara condensation / 3.1: Petasis-Tebbe reaction / 4.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ja060369+