methyl (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoate

Base Information

• Chemical Name: methyl (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoate
• CAS No.: 111661-02-0
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.257
• Mol file: 111661-02-0.mol

Synonyms:(3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoic acid methyl ester

Chemical Property of methyl (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoate

There total 35 articles about methyl (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoate 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: 100.0%

methyl 2,2-dimethyl-3-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate → methyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate (61866-20-4,111661-02-0,149885-37-0,35022-33-4)

Guidance literature:

With sodium perborate tetrahydrate; In tetrahydrofuran; water; at 28 ℃; for 12h; Inert atmosphere;

DOI:10.1039/c8ob02469c

Reference yield: 98.0%

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) + benzaldehyde (100-52-7) → methyl 3-hydroxy-2,2-dimethyl-3-phenylpropanoate (61866-20-4,111661-02-0,149885-37-0,35022-33-4)

Guidance literature:

With lithium benzyloxide; In N,N-dimethyl-formamide; at -45 ℃; for 3h; Further Variations:; Reagents; Product distribution;

DOI:10.1002/adsc.200404084

Reference yield: 95.0%

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene (31469-15-5) + benzaldehyde (100-52-7) → (3R)-3-hydroxy-2,2-dimethyl-3-phenylpropanoic acid methyl ester (111661-02-0)

Guidance literature:

benzaldehyde; With (NHC₄H₇C(C₆H₃(CH₃)2)2O)BC₆H₅⁽¹⁺⁾*O₃SCF₃^(1-)=[(NHC₄H₇C(C₆H₃(CH₃)2)2O)BC₆H₅](O₃SCF₃); Triphenylphosphine oxide; In toluene; at -40 ℃; for 0.25h; Inert atmosphere;

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; In toluene; at -40 ℃; for 20.3333h; Inert atmosphere;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.25h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ol102234k

upstream raw materials:

methanol

C₁₃H₁₈BBrO₂

1-methoxy-2-methyl-1-trimethylsiloxy-1-propene

benzaldehyde

Downstream raw materials:

(3S)-3-hydroxy-2,2-dimethyl-3-phenylpropanoic acid methyl ester

methyl 3-[(dimethoxyphosphoryl)methoxy]-2,2-dimethyl-3-phenylpropanoate

methyl 3-(methoxymethoxy)-2,2-dimethyl-3-phenylpropanoate

3-methoxy-2,2-dimethyl-3-benzenepropionic acid methyl ester

Refernces

• 1、 Song, Jinhua J.,Tan, Zhulin,Reeves, Jonathan T.,Yee, Nathan K.,Senanayake, Chris H.. "N-heterocyclic carbene-catalyzed Mukaiyama aldol reactions". . p. 1013 - 1016. Retrieved 2007.
• 2、 Wessjohann, Ludger,Wild, Harry. "Excellent Aldehyde and Ketone Selectivity in Chromium(II)-Mediated Reformatsky Reactions". . p. 731 - 733. Retrieved 1997.
• 3、 Nishikido, Joji,Nanbo, Masayuki,Yoshida, Akihiro,Nakajima, Hitoshi,Matsumoto, Yousuke,Mikami, Koichi. "Metallo-enzyme model in pure water: Cyclodextrin-lanthanide tris(perfluoroalkanesulfonyl)methide and bis(perfluoroalkanesulfonyl)amide complexes". . p. 1613 - 1616. Retrieved 2002.
• 4、 Yamashita, Yasuhiro,Salter, Matthew M.,Aoyama, Kayoko,Kobayashi, Shu. "With molecular-oxygen-activated Lewis acids: Dinuclear molybdenum complexes for aza-Diels-Alder reactions of acyl hydrazones". . p. 3816 - 3819. Retrieved 2006.
• 5、 Fujisawa, Hidehiko,Takahashi, Eiki,Mukaiyama, Teruaki. "Lewis base catalyzed mannich-type reactions between trimethylsilyl enol ethers and aldimines". . p. 5082 - 5093. Retrieved 2006.
• 6、 Manabe, Kei,Mori, Yuichiro,Wakabayashi, Takeshi,Nagayama, Satoshi,Kobayashi, Shu. "Organic synthesis inside particles in water: Lewis acid-surfactant-combined catalysts for organic reactions in water using colloidal dispersions as reaction media". . p. 7202 - 7207. Retrieved 2000.
• 7、 Nakagawa, Takashi,Fujisawa, Hidehiko,Mukaiyama, Teruaki. "Lithium acetate-catalyzed aldol reaction between aldehyde and trimethylsilyl enolate". . p. 462 - 463. Retrieved 2003.
• 8、 Yu, Libing,Chen, Depu,Li, Jun,Wang, Peng George. "Preparation, Characterization, and Synthetic Uses of Lanthanide(III) Catalysts Supported on Ion Exchange Resins". . p. 3575 - 3581. Retrieved 1997.
• 9、 Ishihara, Kazuaki,Hanaki, Naoyuki,Funahashi, Miyuki,Miyata, Mayumi,Yamamoto, Hisashi. "Tris(pentafluorophenyl)boron as an Efficient, Air Stable, and Water Tolerant Lewis Acid Catalyst". . p. 1721 - 1730. Retrieved 1995.
• 10、 Mikami, Koichi,Yamanaka, Masahiro,Islam, Md. Nazrul,Kudo, Kenichi,Seino, Nobuko,Shinoda, Masaki. "'Fluorous nanoflow' system for the Mukaiyama aldol reaction catalyzed by the lowest concentration of the lanthanide complex with bis(perfluorooctanesulfonyl)amide ponytail". . p. 10593 - 10597. Retrieved 2003.