(2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Base Information

• Chemical Name: (2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid
• CAS No.: 51829-98-2
• Molecular Formula: C₉H₁₁NO₅
• Molecular Weight: 213.19
• UNII: PJ3TPU9VZQ
• Nikkaji Number: J324.190D
• Mol file: 51829-98-2.mol

Synonyms:PJ3TPU9VZQ;D-Erythro-3,4-dihydroxyphenylserine;(-)-Erythro-3,4-dihydroxyphenylserine;51829-98-2;D-erythro-DOPS;UNII-PJ3TPU9VZQ;SCHEMBL8461926;(2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid;D-Tyrosine, beta,3-dihydroxy-, erythro-;D-TYROSINE, .BETA.,3-DIHYDROXY-, ERYTHRO-

Chemical Property of (2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

Chemical Property:

• Boiling Point: 549.8±50.0 °C(Predicted)
• PKA: 2.09±0.24(Predicted)
• Density: 1.608±0.06 g/cm3(Predicted)
• XLogP3: -3.2
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 213.06372245
• Heavy Atom Count: 15
• Complexity: 235

Purity/Quality:

99% ^*data from raw suppliers

erythro-β,3-Dihydroxy-D-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=C(C=C1C(C(C(=O)O)N)O)O)O
• Isomeric SMILES: C1=CC(=C(C=C1[C@H]([C@H](C(=O)O)N)O)O)O
• Uses: erythro-β,3-Dihydroxy-D-tyrosine as an adrenergic pro-drug. Bioactivation of erythro-β,3-Dihydroxy-D-tyrosine to the potent pharmacological agent, noradrenalone (arterenone), via sequential stereoselective action by two target enzymes - dopamine β-monooxygenase (DBM) and L-arom. amino acid decarboxylase (AADC) - acting in tandem.

Technology Process of (2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid

There total 6 articles about (2R,3R)-2-amino-3-(3,4-dihydroxyphenyl)-3-hydroxypropanoic acid 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:

3,4-dibenzyloxybenzaldehyde (5447-02-9) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: aq.-ethanolic NaOH / anschliessendes Erwaermen mit wss. HCl

2: palladium; aqueous methanol / Hydrogenation

With methanol; sodium hydroxide; palladium;

Reference yield:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine (55449-18-8,55449-19-9,55637-52-0,70543-77-0,70561-66-9,106887-48-3,113139-65-4,124709-63-3,146985-69-5) → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

With methanol; palladium; Hydrogenation;

Reference yield:

(2RS:3SR)-2-amino-3-hydroxy-3-(3,4-bis-ethoxycarbonyloxy-phenyl)-propionic acid ethyl ester → (+/-)-threo-DOPS (492-46-6,3916-18-5,6204-89-3,13147-26-7,16322-99-9,23651-95-8,34047-62-6,34124-73-7,50731-20-9,51829-98-2,51829-99-3,89886-54-4)

Guidance literature:

With alkaline solution;

upstream raw materials:

D,L-threo-3-(3,4-Dibenzyloxyphenyl)serine

3,4-dibenzyloxybenzaldehyde

3,4-bis(ethoxycarboxy)-benzaldehyde

(2RS.3RS)-2-amino-3-(3,4-bis-benzyloxy-phenyl)-3-hydroxy-propionic acid