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

Base Information

• Chemical Name: (2RS,4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsiloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane
• CAS No.: 460745-04-4
• Molecular Formula: C₃₁H₅₂O₄Si
• Molecular Weight: 516.837
• Mol file: 460745-04-4.mol

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

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

There total 1 articles about (2RS,4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsiloxy)-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:

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:

(2RS,4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsiloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (460745-04-4) → (4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsilyloxy)-3'-hydroxyoctadecanyl]-2-phenyl-1,3-dioxolane (636596-82-2)

Guidance literature:

With hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 2.5h;

DOI:10.1002/chem.200305185

Reference yield:

(2RS,4S)-4-[(3'S,4'R)-4'-(tert-butyldimethylsiloxy)-3'-hydroxy-1'-hexadecynyl]-2-phenyl-1,3-dioxolane (460745-04-4) → Toluene-4-sulfonic acid (1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-1-((S)-3,4-dihydroxy-butyl)-tetradecyl ester

Guidance literature:

Multi-step reaction with 3 steps

1: H₂; Et₃N / Pd/C / ethyl acetate / 2.5 h / 20 °C

2: pyridine / 7 h / 20 °C

3: H₂ / Pd/C / ethyl acetate / 24 h / 20 °C

With pyridine; hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate;

DOI:10.1002/chem.200305185

upstream raw materials:

benzaldehyde dimethyl acetal

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

(R)-2-hydroxytetradecanal tert-butyldimethylsilyl ether

Downstream raw materials:

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

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

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