(R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal

Base Information

• Chemical Name: (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal
• CAS No.: 920034-28-2
• Molecular Formula: C₅₈H₈₃NO₁₀Si₂
• Molecular Weight: 1010.47
• Mol file: 920034-28-2.mol

Synonyms:(R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal

Chemical Property of (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal

There total 32 articles about (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal 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: 86.0%

(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-hydroxyethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal (920034-40-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal (920034-28-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; for 12h;

DOI:10.1021/ol062531j

Reference yield:

2-(2-hydroxy-ethyl)-3,5-dimethyl-6-[1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-tetrahydro-pyran-4-ol (920034-38-4) → (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal (920034-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 99 percent / N,N-diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 12 h

2.1: sodium hydride / tetrahydrofuran / 15 h / Heating

2.2: 95 percent / tetrahydrofuran / 4.5 h / Heating

3.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 °C

3.2: 96 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C

4.1: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 1 h

5.1: 84 percent / manganese dioxide / CH₂Cl₂ / 2 h

6.1: 86 percent / imidazole / CH₂Cl₂ / 12 h

With 1H-imidazole; dmap; manganese(IV) oxide; sodium hydride; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ol062531j

Reference yield:

(2R,3R,4S,5R,6R,E)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3,5-dimethyl-6-(1-(2-methyloxazol-4-yl)prop-1-en-2-yl)-tetrahydro-2H-pyran-4-ol (920034-37-3) → (R,E)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2Hpyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-4-(tert-butyldiphenylsilanyloxy)-2-methylbut-2-enal (920034-28-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydride / tetrahydrofuran / 15 h / Heating

1.2: 95 percent / tetrahydrofuran / 4.5 h / Heating

2.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 °C

2.2: 96 percent / tetrahydrofuran; hexane / 0.67 h / -78 °C

3.1: 99 percent / p-toluenesulfonic acid monohydrate / methanol / 1 h

4.1: 84 percent / manganese dioxide / CH₂Cl₂ / 2 h

5.1: 86 percent / imidazole / CH₂Cl₂ / 12 h

With 1H-imidazole; manganese(IV) oxide; sodium hydride; toluene-4-sulfonic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; hexane; dichloromethane;

DOI:10.1021/ol062531j

upstream raw materials:

(R,E)-4-(tert-butyldiphenylsilanyloxy)-4-((2R,4R,6S)-6-((4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-hydroxyethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazol-2-yl)methyl)-4,6-dimethoxytetrahydro-2H-pyran-2-yl)-2-methylbut-2-enal

tert-butyldimethylsilyl chloride

2-(2-hydroxy-ethyl)-3,5-dimethyl-6-[1-methyl-2-(2-methyl-oxazol-4-yl)-vinyl]-tetrahydro-pyran-4-ol

(2R,3R,4S,5R,6R,E)-2-(2-(tert-butyldimethylsilyloxy)ethyl)-3,5-dimethyl-6-(1-(2-methyloxazol-4-yl)prop-1-en-2-yl)-tetrahydro-2H-pyran-4-ol

Downstream raw materials:

2-(((2S,4R,6R)-6-((1R,2E,4E,6R,8E)-9-bromo-1-(tert-butyldiphenylsilanyloxy)-6-methoxy-3-methylnona-2,4,8-trienyl)-2,4-dimethoxytetrahydro-2Hpyran-2-yl)methyl)-4-((E)-2-((2R,3R,4S,5S,6R)-6-(2-(tert-butyldimethylsilanyloxy)ethyl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)prop-1-enyl)oxazole

2-((2R,3S,4S,5R,6R)-6-((E)-1-(2-(((2S,4R,6R)-6-((1R,2E,4E,6R,8E)-9-bromo-1-(tert-butyldiphenylsilanyloxy)-6-methoxy-3-methylnona-2,4,8-trienyl)-2,4-dimethoxytetrahydro-2H-pyran-2-yl)methyl)oxazol-4-yl)prop-1-en-2-yl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)acetaldehyde

2-((2R,3S,4S,5R,6R)-6-((E)-1-(2-(((2S,4R,6R)-6-((1R,2E,4E,6R,8E)-9-bromo-1-(tert-butyldiphenylsilanyloxy)-6-methoxy-3-methylnona-2,4,8-trienyl)-2,4-dimethoxytetrahydro-2H-pyran-2-yl)methyl)oxazol-4-yl)prop-1-en-2-yl)-4-(4-methoxybenzyloxy)-3,5-dimethyltetrahydro-2H-pyran-2-yl)ethanol