N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine

Base Information

• Chemical Name: N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine
• CAS No.: 65564-08-1
• Molecular Formula: C₁₃H₁₈N₂O₅
• Molecular Weight: 282.296

Synonyms:N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine

Chemical Property of N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine

Chemical Property:

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Technology Process of N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine

There total 21 articles about N^δ-benzyloxycarbonyl-threo-β-hydroxy-L-ornithine 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: 87.0%

erythro-N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester hydrochloride (114350-18-4,114350-19-5,130712-42-4,130712-43-5) → Nδ-benzyloxycarbonyl-erythro-β-hydroxy-DL-ornithine (65564-06-9,65564-08-1,73870-55-0,73883-84-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1039/P19900001521

Reference yield: 67.0%

threo-N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester (116108-48-6,116108-51-1,116128-50-8) → Nδ-benzyloxycarbonyl-threo-β-hydroxy-DL-ornithine (65564-06-9,65564-08-1,73870-55-0,73883-84-8)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1039/P19900001521

Reference yield: 10.1%

3-[(benzyloxycarbonyl)amino]propanal (65564-05-8) + copper(II) glycinate (32817-15-5) → Nδ-benzyloxycarbonyl-erythro-β-hydroxy-DL-ornithine (65564-06-9,65564-08-1,73870-55-0,73883-84-8) + Nδ-benzyloxycarbonyl-threo-β-hydroxy-DL-ornithine (65564-06-9,65564-08-1,73870-55-0,73883-84-8)

Guidance literature:

With sodium carbonate; In dichloromethane; at 60 ℃; for 1.5h; Yields of byproduct given;

DOI:10.1246/bcsj.53.508

upstream raw materials:

3-[(benzyloxycarbonyl)amino]propanal

copper(II) glycinate

erythro-N⁵-benzyloxycarbonyl-3-hydroxyornithine benzyl ester hydrochloride

phenylmethyl [3,3-bis(ethyloxy)propyl]carbamate

Downstream raw materials:

(2S,3R)-N⁵-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate

N^α , N^δ-bis(benzyloxycarbonyl)-threo-β-hydroxy-L-ornithine

(2S,3R)-N⁵-benzyloxycarbonyl-3-hydroxyornithine benzyl ester

(2S,3R)-N⁵-benzyloxycarbonyl-N²-(2-carboxyethyl)-3-hydroxyornithine benzyl ester

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