(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane

Base Information

• Chemical Name: (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane
• CAS No.: 929915-17-3
• Molecular Formula: C₃₁H₅₂O₄Si
• Molecular Weight: 516.837
• Mol file: 929915-17-3.mol

Synonyms:(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane

Chemical Property of (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane

There total 6 articles about (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane 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: 96.0%

benzaldehyde dimethyl acetal (1125-88-8) + (S)-but-3-yne-1,2-diol (131905-86-7) + (R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether (114379-26-9) → (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (929915-17-3)

Guidance literature:

benzaldehyde dimethyl acetal; (S)-but-3-yne-1,2-diol; With camphor-10-sulfonic acid; In tetrahydrofuran; Heating;

(R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether; With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; Further stages.;

DOI:10.1021/ol026393j

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + (S)-but-3-yne-1,2-diol (131905-86-7) + (R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether (114379-26-9) → (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (929915-17-3) + (2RS,4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsiloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (460745-04-4)

Guidance literature:

benzaldehyde dimethyl acetal; (S)-but-3-yne-1,2-diol; With camphor-10-sulfonic acid; In tetrahydrofuran; Heating;

With (1S,2R)-(+)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 0.25h;

(R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether; In toluene; at 20 ℃; for 116h; Further stages. Title compound not separated from byproducts.;

DOI:10.1021/ol026393j

Reference yield:

(R)-tetradecane-1,2-diol (153062-86-3) → (4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (929915-17-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / CH₂Cl₂ / 0 - 20 °C

2.1: imidazole / dimethylformamide / 0 - 20 °C

3.1: DIBAL-H / CH₂Cl₂ / -78 °C

4.1: Dess-Martin periodinane / CH₂Cl₂ / 20 °C

5.1: CSA / tetrahydrofuran / Heating

5.2: 96 percent / (1R,2S)-N-methylephedrine; Zn(OTf)2; Et₃N / toluene / 20 °C

With pyridine; 1H-imidazole; camphor-10-sulfonic acid; diisobutylaluminium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol026393j

upstream raw materials:

benzaldehyde dimethyl acetal

(S)-but-3-yne-1,2-diol

(R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether

(R)-tetradecane-1,2-diol

Downstream raw materials:

(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxyoctadecanyl]-2-phenyl-1,3-dioxolane

(2S,5R,6R)-6-(tert-butyldimethylsilyloxy)-2,5-dihydroxyoctadecanyl 2',4',6'-triisopropylbenzenesulfonate

(4S)-4-[(3'R,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-(p-toluenesulfonyloxy)octadecanyl]-2-phenyl-1,3-dioxolane

Toluene-4-sulfonic acid (1R,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-3,4-dihydroxy-butyl)-tetradecyl ester