N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester

Base Information

• Chemical Name: N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester
• CAS No.: 112335-66-7
• Molecular Formula: C₃₂H₄₅N₃O₇
• Molecular Weight: 583.725

Synonyms:N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester

Chemical Property of N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester

Chemical Property:

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Technology Process of N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester

There total 1 articles about N^α-butyloxycarbonyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester 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: 74.0%

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) + Thr(Bzl)-Phe-OMe hydrochloride (40162-63-8) → Nα-butyloxycarbonyl-L-leucyl-Oβ-benzyl-L-threonyl-L-phenylalanine methyl ester (112335-66-7)

Guidance literature:

With 1-hydroxy-pyrrolidine-2,5-dione; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane;

Reference yield: 89.0%

Nα-butyloxycarbonyl-L-leucyl-Oβ-benzyl-L-threonyl-L-phenylalanine methyl ester (112335-66-7) → (S)-2-[(2S,3R)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-benzyloxy-butyrylamino]-3-phenyl-propionic acid methyl ester (112335-69-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; for 0.5h; Ambient temperature;

Reference yield:

Nα-butyloxycarbonyl-L-leucyl-Oβ-benzyl-L-threonyl-L-phenylalanine methyl ester (112335-66-7) → periplanetin CC-2 (93240-39-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 89 percent / 1 N aq. HCl / dioxane / 0.5 h / Ambient temperature

2: triethylamine (TEA) / CHCl₃

3: 2 g / H₂, 5percent aq. CH₃COOH / 10percent Pd/BaSO₄ / methanol

4: 30 percent / hydrazine hydrate / methanol / 5 h / 4 °C

5: 1.) amyl nitrite, 4 N aq. HCl / 1.) dioxane, 2.) DMF, dioxane

With hydrogenchloride; n-Amyl nitrite; hydrogen; hydrazine hydrate; acetic acid; triethylamine; Pd-BaSO₄; In 1,4-dioxane; methanol; chloroform;

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

Thr(Bzl)-Phe-OMe hydrochloride

Downstream raw materials:

(S)-2-[(2S,3R)-2-((S)-2-Amino-4-methyl-pentanoylamino)-3-benzyloxy-butyrylamino]-3-phenyl-propionic acid methyl ester

(S)-5-Oxo-pyrrolidine-2-carboxylic acid {(S)-1-[(1S,2R)-1-((S)-1-hydrazinocarbonyl-2-phenyl-ethylcarbamoyl)-2-hydroxy-propylcarbamoyl]-3-methyl-butyl}-amide

N-benzyloxycarbonyl-α-pyroglutamyl-L-leucyl-O^β-benzyl-L-threonyl-L-phenylalanine methyl ester

periplanetin CC-2

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