(+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Base Information

• Chemical Name: (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate
• CAS No.: 136749-45-6
• Molecular Formula: C₁₀H₁₂O₅
• Molecular Weight: 212.202
• Mol file: 136749-45-6.mol

Synonyms:(+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Chemical Property of (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

There total 7 articles about (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate 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: 95.0%

(-)-(S)-methyl 3-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-2-hydroxypropanoate → (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (136749-45-6)

Guidance literature:

With triethylamine hydrofluoride; In pyridine; at 20 ℃; for 0.5h; optical yield given as %ee; Inert atmosphere;

DOI:10.1002/ejoc.201200689

Reference yield:

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride (32404-28-7) → (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (136749-45-6)

Guidance literature:

Multi-step reaction with 4 steps

1: NaNO₂ / H₂O / 24 h / Ambient temperature

2: CHCl₃ / 12 h / Heating; strongly acidic ion exchanger

3: 5 N NaOH, 30percent H₂O₂ / H₂O / 0.5 h / 40 °C

4: HCl-gas / 12 h / Heating

With hydrogenchloride; sodium hydroxide; dihydrogen peroxide; sodium nitrite; In chloroform; water;

Reference yield:

(-)-(2S,3R)-methyl (3-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]-2,3-dihydroxy)propanoate → (+)-(S)-methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (136749-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 2 h / -78 °C / Inert atmosphere

2: triethylamine hydrofluoride / pyridine / 0.5 h / 20 °C / Inert atmosphere

With triethylsilane; boron trifluoride diethyl etherate; triethylamine hydrofluoride; In pyridine; dichloromethane;

DOI:10.1002/ejoc.201200689

upstream raw materials:

methanol

(2S)-3-(3,4-dihydroxyphenyl)-2-hydroxypropionic acid

(S)-3-(3-ACETYL-4-HYDROXY-PHENYL)-2-HYDROXY-PROPIONIC ACID

3-(3'-acetyl-4'-hydroxyphenyl)-(S)-lactic acid ethyl ester

Downstream raw materials:

(1R/S,3S)-Methyl-3,4-dihydro-6,7-dihydroxy-1-(2-menthyloxycarbonylethyl)-1-methyl-1H-2-benzopyran-3-carboxylat

(S)-3-(3,4-Dihydroxy-phenyl)-2-hydroxy-N-((R)-1-phenyl-ethyl)-propionamide

Methyl (S)-(+)-3-(3,4 dimethoxyphenyl)-2-hydroxypropionate

(R)-methyl 3-(3,4-bis(benzyloxy)phenyl)-2-hydroxypropanoate

Refernces

• 1、 Wuensch, Bernhard,Zott, Matthias. "Chiral 2-Benzopyran-3-carboxylates by Oxa-Pictet-Spengler Reaction of (S)-3-Phenyllactic Acid Derivatives". . p. 39 - 46. Retrieved 2007/10/02.