(R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester

Base Information

• Chemical Name: (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester
• CAS No.: 339201-14-8
• Molecular Formula: C₂₃H₂₄N₂O₆
• Molecular Weight: 424.453

Synonyms:(R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester

Chemical Property of (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester

There total 2 articles about (R)-N-benzyloxycarbonyl-N-phthalimidoleucine 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: 97.0%

N-benzyloxycarbonylaminophthalimide (287728-91-0) + methyl (2S)-2-hydroxy-4-methylpentanoate (17392-84-6) → (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester (339201-14-8)

Guidance literature:

With dialkylazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2006.12.085

Reference yield:

L-leucine (61-90-5,21675-61-6,25248-98-0,70-45-1) → (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester (339201-14-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaNO₂; CH₃COOH

1.2: SOCl₂

2.1: 97 percent / triphenylphosphine; dialkylazodicarboxylate / tetrahydrofuran / 3 h / 20 °C

With dialkylazodicarboxylate; acetic acid; triphenylphosphine; sodium nitrite; In tetrahydrofuran; 2.1: Mitsunobu reaction;

DOI:10.1016/j.tet.2006.12.085

Reference yield: 100.0%

pyrrolidine (123-75-1) + (R)-N-benzyloxycarbonyl-N-phthalimidoleucine methyl ester (339201-14-8) → 2-{N-benzyloxycarbonyl-N'-[2-(pyrrolidine-1-carbonyl)-benzoyl]-hydrazino}-4-methyl-pentanoic acid methyl ester (929720-00-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2006.12.085

upstream raw materials:

N-benzyloxycarbonylaminophthalimide

methyl (2S)-2-hydroxy-4-methylpentanoate

L-leucine

Downstream raw materials:

2-{N-benzyloxycarbonyl-N'-[2-(pyrrolidine-1-carbonyl)-benzoyl]-hydrazino}-4-methyl-pentanoic acid methyl ester

C₂₀H₃₀N₂O₆

C₃₂H₄₁N₃O₈

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