ethyl (2S)-2-hydroxy-2-methyl-3-phenylpropanoate

Base Information

• Chemical Name: ethyl (2S)-2-hydroxy-2-methyl-3-phenylpropanoate
• CAS No.: 285130-47-4
• Molecular Formula: C12H16 O3
• Molecular Weight: 208.257
• DSSTox Substance ID: DTXSID20472684
• Nikkaji Number: J2.692.359J
• Wikidata: Q82301742
• Mol file: 285130-47-4.mol

Synonyms:285130-47-4;ethyl (2S)-2-hydroxy-2-methyl-3-phenylpropanoate;ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE;DTXSID20472684;(S)-ETHYL 2-HYDROXY-2-METHYL-3-PHENYLPROPANOATE

Chemical Property of ethyl (2S)-2-hydroxy-2-methyl-3-phenylpropanoate

Chemical Property:

• PSA: 46.53000
• LogP: 1.54320
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 208.109944368
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

98%min ^*data from raw suppliers

(S)-2-HYDROXY-2-METHYL-3-PHENYLPROPIONIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(C)(CC1=CC=CC=C1)O
• Isomeric SMILES: CCOC(=O)[C@](C)(CC1=CC=CC=C1)O

Technology Process of ethyl (2S)-2-hydroxy-2-methyl-3-phenylpropanoate

There total 4 articles about ethyl (2S)-2-hydroxy-2-methyl-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: 93.0%

ethyl (2S,3R)-2,3-dihydroxy-2-methyl-3-phenylpropanoate (1115955-24-2) → ethyl (S)-2-hydroxy-2-methyl-3-phenylpropanoate (285130-47-4,205505-45-9)

Guidance literature:

ethyl (2S,3R)-2,3-dihydroxy-2-methyl-3-phenylpropanoate; With trifluoroacetic anhydride; at 20 ℃; for 0.5h;

With 10% Pd/C; hydrogen; In ethanol; at 20 ℃; optical yield given as %ee;

DOI:10.1021/ol802325h

Reference yield: 83.0%

ethanol (64-17-5) + (S)-2-Hydroxy-2-methyl-4-phenylpropanenitrile (219616-61-2) → ethyl (S)-2-hydroxy-2-methyl-3-phenylpropanoate (285130-47-4,205505-45-9)

Guidance literature:

With hydrogenchloride; at 90 - 100 ℃; for 16h;

DOI:10.1002/1521-3765(20000717)6:14<2564::AID-CHEM2564>3.0.CO;2-F

Reference yield: 66.0%

ethanol (64-17-5) + (2S,5S)-5-benzyl-2-(t-butyl)-5-methyl-1,3-dioxolan-4-one (92572-43-5) → ethyl (S)-2-hydroxy-2-methyl-3-phenylpropanoate (285130-47-4,205505-45-9)

Guidance literature:

With sodium ethanolate; for 0.166667h; Heating;

DOI:10.1016/S0968-0896(00)00006-7

upstream raw materials:

ethanol

(2S,5S)-5-benzyl-2-(t-butyl)-5-methyl-1,3-dioxolan-4-one

(S)-2-Hydroxy-2-methyl-4-phenylpropanenitrile

1-phenyl-acetone

Downstream raw materials:

ethyl (R)-2-azido-2-methyl-3-phenylpropanoate

(S)-benzyl hippuryl-α-methylphenyllactate

(S)-benzyl t-Boc-glycyl-α-methylphenyllactate

(S)-Hippuryl-alpha-methylphenyllactic acid