(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

Base Information

• Chemical Name: (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde
• CAS No.: 863604-39-1
• Molecular Formula: C₃₀H₅₄O₃Si₂
• Molecular Weight: 518.928
• Mol file: 863604-39-1.mol

Synonyms:(2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

Chemical Property of (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde

There total 4 articles about (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde 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: 99.0%

(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol (863604-46-0) → (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde (863604-39-1)

Guidance literature:

With pyridine-SO₃ complex; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo0511290

Reference yield:

(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran (863604-38-0) → (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde (863604-39-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Pd(OH)2; H₂ / tetrahydrofuran / 2 h / 20 °C

2: diisopropylethyl amine; DMSO; SO₃*pyridine / CH₂Cl₂ / 1 h / 0 °C

With palladium dihydroxide; pyridine-SO₃ complex; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2: Parikh-Doering oxidation;

DOI:10.1021/ja051986l

Reference yield:

allyldimethylphenylsilane (18001-18-8) → (2R,4R,5S)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-carbaldehyde (863604-39-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: t-BuOK; n-BuLi / tetrahydrofuran; hexane / -78 - -45 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: BF₃*Et₂O / tetrahydrofuran; hexane / 4 h / -78 °C

2.2: imidazole / dimethylformamide / 48 h / 50 °C

2.3: 1.2 g / SnCl₄ / CH₂Cl₂ / 20 h / -45 °C

3.1: 87 percent / H₂ / Pd(OH)2/C / tetrahydrofuran / 2 h / 20 °C

4.1: 99 percent / SO₃*pyridine; DMSO; (i-Pr)2NEt / CH₂Cl₂ / 1 h / 0 °C

With n-butyllithium; pyridine-SO₃ complex; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo0511290

upstream raw materials:

(2R,4R,5S)-[5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-4-(dimethylphenylsilanyl)tetrahydrofuran-2-yl]methanol

(2S,3R,5R)-5-(benzyloxymethyl)-2-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-3-(dimethylphenylsilanyl)tetrahydrofuran

allyldimethylphenylsilane

[(E)-γ-(dimethylphenylsilyl)allyl]diisopinocamphenylborane

Downstream raw materials:

(+)-asimicin

(2R,2'R,4R,4'R,5S,5'S)-4,4'-bis-(dimethylphenylsilanyl)-5-[(1R)-1-(tert-butyldimethylsilanyloxy)undecyl]-5'-[(1R,12R,16R)-1,12-bis-(tert-butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)heptadec-14-yne]octahydro-2,2'-bifuran