(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

Base Information

• Chemical Name: (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
• CAS No.: 853995-90-1
• Molecular Formula: C₂₇H₄₃BrO₅Si
• Molecular Weight: 555.625
• Mol file: 853995-90-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 14 articles about (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 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: 85.0%

{3-Bromo-4,6-dimethoxy-5-methyl-2-[(2R,5S,6R)-5-methyl-4-methylene-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-2-yl]-phenoxy}-tert-butyl-dimethyl-silane (853995-89-8) → (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 (853995-90-1)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; at -78 ℃; for 0.166667h;

DOI:10.1021/ja051420x

Reference yield:

2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde (853995-97-8) → (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 (853995-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / diisopropylethylamine / dimethylformamide / 1.5 h / 20 °C

2: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

3: 85 percent / tetrahydrofuran / 24 h / Heating

4: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

With isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Kurihara condensation / 3: Petasis-Tebbe reaction / 4: Petasis-Ferrier rearrangement;

DOI:10.1021/ja060369+

Reference yield:

2-bromo-6-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethoxy-4-methyl-benzaldehyde (853995-87-6) → (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 (853995-90-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 77 percent / i-PrOTMS; TMSOTf / CH₂Cl₂ / -78 °C

2: 85 percent / tetrahydrofuran / 24 h / Heating

3: 85 percent / Me₂AlCl / CH₂Cl₂ / 0.17 h / -78 °C

With isopropoxytrimethylsilane; trimethylsilyl trifluoromethanesulfonate; dimethylaluminum chloride; In tetrahydrofuran; dichloromethane; 1: Kurihara condensation / 2: Petasis-Tebbe reaction / 3: Petasis-Ferrier rearrangement;

DOI:10.1021/ja060369+

upstream raw materials:

{3-Bromo-4,6-dimethoxy-5-methyl-2-[(2R,5S,6R)-5-methyl-4-methylene-6-((S)-3-methyl-pent-4-enyl)-[1,3]dioxan-2-yl]-phenoxy}-tert-butyl-dimethyl-silane

(2S,3R,6S)-3-Hydroxy-2,6-dimethyl-oct-7-enoic acid

2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde

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

Downstream raw materials:

(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,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

(2R,3S,4S,5S,6R)-2-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyl-6-((S)-3-methylpent-4-enyl)-tetrahydropyran

(3S,5S)-1-{3-(tert-Butyl-dimethyl-silanyloxy)-2-[(2R,3S,4S,5S,6R)-4-(tert-butyl-dimethyl-silanyloxy)-3,5-dimethyl-6-((S)-3-methyl-pent-4-enyl)-tetrahydro-pyran-2-yl]-4,6-dimethoxy-5-methyl-phenyl}-3,5,7-trimethyl-oct-7-en-2-ol