Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate

Base Information

• Chemical Name: Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate
• CAS No.: 159848-77-8
• Molecular Formula: C₁₂H₁₆O₅
• Molecular Weight: 240.256
• DSSTox Substance ID: DTXSID601210923
• Nikkaji Number: J768.742G
• Mol file: 159848-77-8.mol

Synonyms:159848-77-8;SCHEMBL6872391;DTXSID601210923;Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate;(alphaS,betaR)-alpha,beta-Dihydroxy-4-methoxybenzenepropionic acid ethyl ester

Chemical Property of Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate

Chemical Property:

• XLogP3: 0.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 240.09977361
• Heavy Atom Count: 17
• Complexity: 235

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate

There total 9 articles about Ethyl (alphaS,betaR)-alpha,beta-dihydroxy-4-methoxybenzenepropanoate 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: 94.0%

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate (24393-56-4) → ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (159848-77-8)

Guidance literature:

With osmium(VIII) oxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In water; tert-butyl alcohol; at 0 ℃; for 16h;

DOI:10.1016/j.tetlet.2004.07.157

Reference yield: 93.0%

para-iodoanisole (696-62-8) + ethyl acrylate (140-88-5,9003-32-1) → ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (159848-77-8)

Guidance literature:

para-iodoanisole; ethyl acrylate; With triethylamine; LDH-PdOsW; at 70 ℃;

With 4-methyl-morpholine; (3a,9R,3'''a,4'"b,9'"R)-9,9'-[1,4-phthalazinediylbis(oxy)]bis[6'-(methyloxy)-10,11-dihydrocinchonan]; dihydrogen peroxide; LDH-PdOsW; In tert-butyl alcohol; at 20 ℃; for 1h; Further stages.;

DOI:10.1021/jo026687i

Reference yield: 86.0%

(2S,3R)-3-Acetoxy-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid ethyl ester (182187-05-9) → ethyl (2S,3R)-2,3-dihydroxy-3-(4-methoxyphenyl)propanoate (159848-77-8)

Guidance literature:

With potassium carbonate; In ethanol; for 3h; Ambient temperature;

DOI:10.1021/jo960835l

upstream raw materials:

ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate

(2S,3R)-3-Acetoxy-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid ethyl ester

para-iodoanisole

ethyl acrylate

Downstream raw materials:

ethyl (2S,3R)-3-hydroxy-3-(4-methoxyphenyl)-2-(((4-nitrophenyl)sulfonyl)oxy)propanoate

(2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(toluene-4-sulfonyloxy)-propionic acid ethyl ester

(4S,5R)-trans-5-(4-methoxyphenyl)-2,2-dimethyl-1,3-dioxolan-4-carbaldehyde

(3S,3'S)-3--3-(4-methoxyphenyl)-1-(2,2,2-trichloroethoxycarbonyloxy)propane