(S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid

Base Information

• Chemical Name: (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid
• CAS No.: 78088-92-3
• Molecular Formula: C₃₁H₂₉NO₆
• Molecular Weight: 511.574
• Mol file: 78088-92-3.mol

Synonyms:(S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid

Chemical Property of (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid

There total 10 articles about (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic 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: 78.0%

O-Benzyl-L-serine (4726-96-9,32520-12-0) + 2,3-bis(benzyloxy)benzoyl chloride (69146-58-3) → (R)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (78088-92-3) + (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (78088-92-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; Title compound not separated from byproducts; 1.) 1h, 0 deg C, 2.) 2h, r.t.;

DOI:10.1021/jo00331a001

Reference yield: 78.0%

O-Benzyl-L-serine (4726-96-9,32520-12-0) + 2,3-bis(benzyloxy)benzoyl chloride (69146-58-3) → (R)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (78088-92-3) + (S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (78088-92-3)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; Title compound not separated from byproducts; 1.) 1h, 0 deg C, 2.) 2h, r.t.;

DOI:10.1021/jo00331a001

Reference yield:

2,3-bis(benzyloxy)benzaldehyde (5779-91-9) → (R)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (78088-92-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / H₂NSO₃H, NaClO₂ / acetone; H₂O / 1 h / Ambient temperature

2: 94 percent / oxalyl chloride / DMF / benzene / 0.5 h / 5 °C

3: NaOH / H₂O; tetrahydrofuran / 1.) 1h, 0 deg C, 2.) 2h, r.t.

With sodium hydroxide; sodium chlorite; oxalyl dichloride; aminosulfonic acid; N,N-dimethyl-formamide; In tetrahydrofuran; water; acetone; benzene;

DOI:10.1021/jo00331a001

upstream raw materials:

O-Benzyl-L-serine

2,3-bis(benzyloxy)benzoyl chloride

2,3-bis(benzyloxy)benzaldehyde

2,3-dihydroxybenzaldehyde

Downstream raw materials:

2,3-Dihydroxy-N-benzoyl-serin

2,3-dihydroxybenzoyl-D-serine

(S)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (S)-2-(2,3-bis-benzyloxy-benzoylamino)-2-[2-(4-bromo-phenyl)-2-oxo-ethoxycarbonyl]-ethyl ester

(R)-3-Benzyloxy-2-(2,3-bis-benzyloxy-benzoylamino)-propionic acid (S)-2-(2,3-bis-benzyloxy-benzoylamino)-2-[2-(4-bromo-phenyl)-2-oxo-ethoxycarbonyl]-ethyl ester