(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

Base Information

Chemical Name:(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
CAS No.:853996-00-6
Molecular Formula:C₂₈H₄₅BrO₅Si
Molecular Weight:569.652
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 15 articles about (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 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: 70.0%

: 853995-90-1
(2R,3S,6R)-6-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3-methyl-2-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-one

: 74-88-4
methyl iodide

: 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

Guidance literature:: (2R,3S,6R)-6-[2-Bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-phenyl]-3-methyl-2-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-4-one; With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 - -10 ℃; for 1.5h;

methyl iodide; In tetrahydrofuran; hexane; at -20 - 0 ℃; for 3h;
DOI:10.1021/ja051420x

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

With isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 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:

: 853995-87-6
2-bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-benzaldehyde

: 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

Guidance literature:: Multi-step reaction with 4 steps

1.1: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

2.1: 85 percent / tetrahydrofuran / 24 h / Heating

3.1: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

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

4.2: 70 percent / tetrahydrofuran; hexane / 3 h / -20 - 0 °C

With isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; 1.1: Kurihara condensation / 2.1: Petasis-Tebbe reaction / 3.1: Petasis-Ferrier rearrangement;
DOI:10.1021/ja060369+