ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate

Base Information

• Chemical Name: ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate
• CAS No.: 195375-00-9
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 195375-00-9.mol

Synonyms:ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate

Chemical Property of ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate

There total 6 articles about ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate 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:

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene (31469-16-6) + (4S,5R)-4,5-Dimethyl-2-phenylethynyl-[1,3]dioxolane → ethyl (3S,1'S,2'R)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate + ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate (195375-00-9)

Guidance literature:

With N-tosyl phenylalanine-derived phenylboron; In dichloromethane; at -78 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja9702881

Reference yield:

phenylpropargyl aldehyde diethyl acetal (6142-95-6) → ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate (195375-00-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 49 percent / p-toluenesulfonic acid monohydrate / toluene / 4 h / 100 °C

2: (S)-oxazaborolinine / CH₂Cl₂ / 4 h / -20 °C

With (S)-oxazaborolinine; toluene-4-sulfonic acid; In dichloromethane; toluene; 1: Condensation / 2: Ring cleavage;

DOI:10.1021/jo991071n

Reference yield:

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene (31469-16-6) + rel-(2R,3S,4R)-4,5-dimethyl-2-phenylethylnyl-1,3-dioxolane (251481-79-5) → ethyl (3S,1'S,2'R)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate + ethyl (3R,1'R,2'S)-3-(2'-hydroxy-1'-methylpropyloxy)-2,2-dimethyl-5-phenyl-4-pentynoate (195375-00-9)

Guidance literature:

With (S)-oxazaborolinine; In dichloromethane; at -20 ℃; for 4h; Title compound not separated from byproducts;

DOI:10.1021/jo991071n

upstream raw materials:

1-ethoxy-1-((trimethylsilyl)oxy)-2-methylpropene

rel-(2R,3S,4R)-4,5-dimethyl-2-phenylethylnyl-1,3-dioxolane

rel-(2S,3S,4R)-4,5-dimethyl-2-phenylethylnyl-1,3-dioxolane

phenylpropargyl aldehyde diethyl acetal

Downstream raw materials:

(2R,3S)-3-(benzyloxy)butan-2-ol