Benzeneacetic acid, alpha-amino-3,5-dihydroxy-4-methoxy-, (R)- (9CI)

Base Information

• Chemical Name: Benzeneacetic acid, alpha-amino-3,5-dihydroxy-4-methoxy-, (R)- (9CI)
• CAS No.: 203504-61-4
• Molecular Formula: C9H11 N O5
• Molecular Weight: 213.18734
• Mol file: 203504-61-4.mol

Synonyms:Benzeneaceticacid, a-amino-3,5-dihydroxy-4-methoxy-,(R)- (9CI)

Chemical Property of Benzeneacetic acid, alpha-amino-3,5-dihydroxy-4-methoxy-, (R)- (9CI)

Chemical Property:

• Boiling Point: 493.3±45.0 °C(Predicted)
• PKA: 1.92±0.10(Predicted)
• PSA: 113.01000
• Density: 1.499±0.06 g/cm3(Predicted)
• LogP: 0.89110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzeneacetic acid, alpha-amino-3,5-dihydroxy-4-methoxy-, (R)- (9CI)

There total 15 articles about Benzeneacetic acid, alpha-amino-3,5-dihydroxy-4-methoxy-, (R)- (9CI) 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: 76.0%

4-Methyl-benzenesulfinic acid [(R)-(3,5-bis-benzyloxy-4-methoxy-phenyl)-cyano-methyl]-amide (203504-59-0) → (R)-(-)-(3,5-dihydroxy-4-methoxyphenyl)glycine (203504-61-4,212758-02-6)

Guidance literature:

With hydrogenchloride; In water; at 100 ℃; for 2h;

DOI:10.1021/jo972076s

Reference yield:

(2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid (191542-07-1) → (R)-(-)-(3,5-dihydroxy-4-methoxyphenyl)glycine (203504-61-4,212758-02-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 7h; under 760 Torr;

DOI:10.1055/s-1997-1234

Reference yield:

2-(3,5-bis(benzyloxy)-4-methoxyphenyl)acetic acid (54186-42-4) → (R)-(-)-(3,5-dihydroxy-4-methoxyphenyl)glycine (203504-61-4,212758-02-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Et₃N, trimethylacetyl chloride, 2.) BuLi / 1.) THF, a) -78 deg C, 15 min, b) 0 deg C, 30 min, 2.) THF, hexane, a) -78 deg C, 30 min, b) 0 deg C, 30 min, c) RT, 4 h

2: 1.) KHMDS, 2.) trisyl azide, 3.) glacial AcOH

3: 87 percent / 30percent aq. H₂O₂, aq. LiOH / tetrahydrofuran / 1 h / 0 °C

4: H₂ / 10percent Pd/C / methanol / 7 h / 760 Torr

With lithium hydroxide; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; dihydrogen peroxide; pivaloyl chloride; potassium hexamethylsilazane; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1055/s-1997-1234

upstream raw materials:

(2R)-2-azido-2-[3,5-bis(benzyloxy)-4-methoxyphenyl]ethanoic acid

4-Methyl-benzenesulfinic acid [(R)-cyano-(3,5-diisopropoxy-4-methoxy-phenyl)-methyl]-amide

4-Methyl-benzenesulfinic acid [(R)-(3,5-bis-benzyloxy-4-methoxy-phenyl)-cyano-methyl]-amide

3,5-bis(benzyloxy)-4-methoxybenzaldehyde

Downstream raw materials:

(R)-2-((tert-butoxycarbonyl)amino)-2-(3,5-dihydroxy-4-methoxyphenyl)acetic acid

Refernces

• 1、 Pearson, Anthony J.,Chelliah, Mariappan V.,Bignan, Gilles C.. "Expeditious syntheses of two arylglycine derivatives corresponding to the central amino acid of the vancomycin family of antibiotics". . p. 536 - 540. Retrieved 2007/10/03.