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

Base Information

• Chemical Name: (2S,3R)-N⁵-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate
• CAS No.: 130712-45-7
• Molecular Formula: C₇H₈O₃S*C₂₀H₂₄N₂O₅
• Molecular Weight: 544.626

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 9 articles about (2S,3R)-N⁵-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate 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:

N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester (116108-48-6,116108-51-1,116128-50-8) → (2S,3R)-N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate (130712-45-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1-(3-dimethylaminopropyl)-3-ethyl-carbodi-imide hydrochloride / tetrahydrofuran; CH₂Cl₂ / 2.5 h

2: 78 percent / hydrogen / 10percent Pd/C / ethanol; H₂O / Ambient temperature

3: 35 percent / aq. sodium hydroxide (pH 8-9) / H₂O; methanol / 0.5 h

4: 34 percent / 0.1M sodium hydroxide / H₂O / 3.25 h / 37 °C / resin bound E_. coli acylase

With sodium hydroxide; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water;

DOI:10.1039/P19900001521

Reference yield:

threo-N5-benzyloxycarbonyl-3-hydroxy-N2-phenylacetylornithine benzyl ester (116108-49-7,116108-52-2) → (2S,3R)-N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate (130712-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / hydrogen / 10percent Pd/C / ethanol; H₂O / Ambient temperature

2: 35 percent / aq. sodium hydroxide (pH 8-9) / H₂O; methanol / 0.5 h

3: 34 percent / 0.1M sodium hydroxide / H₂O / 3.25 h / 37 °C / resin bound E_. coli acylase

With sodium hydroxide; hydrogen; palladium on activated charcoal; In methanol; ethanol; water;

DOI:10.1039/P19900001521

Reference yield:

5-azido-N-(diphenylmethylene)-3-hydroxynorvaline ethyl ester → (2S,3R)-N5-benzyloxycarbonyl-3-hydroxyornithine benzyl ester toluene-p-sulphonate (130712-45-7)

Guidance literature:

Multi-step reaction with 6 steps

2: 73 percent / aq. sodium hydroxide / tetrahydrofuran; H₂O / 1 h / Ambient temperature

3: 57 percent / hydrogen / 5percent Pd/C / ethanol; H₂O / Ambient temperature

4: 35 percent / aq. sodium hydroxide (pH 8-9) / H₂O; methanol / 0.5 h

5: 34 percent / 0.1M sodium hydroxide / H₂O / 3.25 h / 37 °C / resin bound E_. coli acylase

With sodium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; water;

DOI:10.1039/P19900001521

upstream raw materials:

p-toluenesulfonic acid monohydrate

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

benzyl bromide

acetoacetic acid methyl ester

Downstream raw materials:

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

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