(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

Base Information

• Chemical Name: (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
• CAS No.: 853995-86-5
• Molecular Formula: C₃₄H₆₁BrO₅Si₂
• Molecular Weight: 685.93
• Mol file: 853995-86-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 18 articles about (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 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: 95.0%

(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 (853996-01-7) + t-butyldimethylsiyl triflate (69739-34-0) → (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 (853995-86-5)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -10 ℃; for 1h;

DOI:10.1021/ja051420x DOI:10.1021/ja060369+

Reference yield: 73.0%

(S)-5-[(2R,3S,4S,5S,6R)-6-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltetrahydropyran-2-yl]-3-methylpentan-1-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 (853995-86-5)

Guidance literature:

(S)-5-[(2R,3S,4S,5S,6R)-6-[2-bromo-6-(tert-butyldimethylsilanyloxy)-3,5-dimethoxy-4-methylphenyl]-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltetrahydropyran-2-yl]-3-methylpentan-1-ol; With ortho-nitrophenyl selenocyanate; tributylphosphine; In tetrahydrofuran;

With dihydrogen peroxide; In tetrahydrofuran; for 2h; Further stages.;

DOI:10.1039/b602937j

Reference yield:

2-bromo-6-hydroxy-3,5-dimethoxy-4-methyl-benzaldehyde (853995-97-8) → (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 (853995-86-5)

Guidance literature:

Multi-step reaction with 7 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

7.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -10 °C

With 2,6-dimethylpyridine; 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+

upstream raw materials:

(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

t-butyldimethylsiyl triflate

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

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

Downstream raw materials:

(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

(5R,6R,7S,8R,9R,12S,13E,16S,18S,19S)-6,7,8,9,10,11,12,15,16,17,18,19-dodecahydro-4,7,19-trihydroxy-2,6,8,12,14,16,18-heptamethyl-1,19:5,9-diepoxybenzo[18]annulen-3(5H)-one