(R)-3-hydroxy-3-phenylbutyric acid methyl ester

Base Information

• Chemical Name: (R)-3-hydroxy-3-phenylbutyric acid methyl ester
• CAS No.: 7210-37-9
• Molecular Formula: C₁₁H₁₄O₃
• Molecular Weight: 194.23
• Mol file: 7210-37-9.mol

Synonyms:(R)-3-hydroxy-3-phenylbutyric acid methyl ester

Chemical Property of (R)-3-hydroxy-3-phenylbutyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (R)-3-hydroxy-3-phenylbutyric acid methyl ester

There total 20 articles about (R)-3-hydroxy-3-phenylbutyric acid methyl ester 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: 80.0%

methanol (67-56-1) + S-tert-butyl (R)-3-hydroxy-3-phenylbutanethioate (1070240-43-5) → (R)-3-hydroxy-3-phenylbutyric acid methyl ester (7210-37-9)

Guidance literature:

With N-Bromosuccinimide; In dichloromethane; at 20 ℃; for 1h; optical yield given as %ee; enantioselective reaction;

DOI:10.1021/ol802087u

Reference yield: 57.0%

methanol (67-56-1) + 3-phenyl-2-butenal (1196-67-4) → (R)-3-hydroxy-3-phenylbutyric acid methyl ester (7210-37-9)

Guidance literature:

With C₁₀H₁₂N₂O₇S; C₂₂H₂₃N₂O⁽¹⁺⁾*Cl^(1-); potassium carbonate; In toluene; at 20 ℃; enantioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/ja511371a

Reference yield:

triethoxyfluorosilane (358-60-1) + [(1-methoxyvinyl)oxy]trimethylsilane (36850-80-3) + acetophenone (98-86-2) → (-)S β-hydroxy β-phenyl n-butanoate de methyle (880-65-9) + (R)-3-hydroxy-3-phenylbutyric acid methyl ester (7210-37-9)

Guidance literature:

triethoxyfluorosilane; acetophenone; With potassium phenyltrifluoborate; (PPh₃)₃CuF; chiral 1-(Cy)2P-2-[2-(Cy)2P-Ph-CHN(nBu)2-]ferrocene; In 1,2-dimethoxyethane; at 20 ℃; for 0.25h;

[(1-methoxyvinyl)oxy]trimethylsilane; In 1,2-dimethoxyethane; at -20 ℃; for 19h;

With triethylamine tris(hydrogen fluoride); In 1,2-dimethoxyethane; at 20 ℃; Title compound not separated from byproducts;

DOI:10.1021/ja061815w

upstream raw materials:

diazomethane

(3R)-3-phenyl-3-hydroxybutanoic acid

(-)S β-hydroxy β-phenyl n-butanoate de methyle

ethyl acetate

Downstream raw materials:

(-)S β-hydroxy β-phenyl n-butanoate de methyle

Refernces

• 1、 Bedná?ová, Eva,Ne?as, David,Císa?ová, Ivana,Du?ek, Michal,Lamaty, Frédéric,Kotora, Martin. "Synthesis of new bipyridine N,N′-dioxides and their application in asymmetric allylation of benzaldehyde and aldol addition to acetophenone". . p. 29 - 48. Retrieved 2018/11/23.
• 2、 Zhang, Yuexia,Du, Yu,Huang, Zhijian,Xu, Jianfeng,Wu, Xingxing,Wang, Yuhuang,Wang, Ming,Yang, Song,Webster, Richard D.,Chi, Yonggui Robin. "N-heterocyclic carbene-catalyzed radical reactions for highly enantioselective β-hydroxylation of enals". supporting information. p. 2416 - 2419. Retrieved 2015/03/04.