(2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid

Base Information

• Chemical Name: (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid
• CAS No.: 1026723-82-9
• Molecular Formula: C₂₀H₃₂N₂O₄
• Molecular Weight: 364.485

Synonyms:(2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid

Chemical Property of (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid

Chemical Property:

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Technology Process of (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid

There total 5 articles about (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic 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: 74.0%

(2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid methyl ester (1027036-48-1) → (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid (1026723-82-9)

Guidance literature:

With lithium hydroxide; In 1,4-dioxane; for 96h; Ambient temperature;

DOI:10.1021/jm970161m

Reference yield:

N-Cbz-L-Isoleucine (3160-59-6) → (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid (1026723-82-9)

Guidance literature:

Multi-step reaction with 4 steps

1: BOP, DIEA / dimethylformamide / 2 h

2: LiAlH₄ / tetrahydrofuran / 0.5 h / 0 °C

3: 74 percent / NaBH₃CN, AcOH / methanol

4: 74 percent / 1M aq. LiOH / dioxane / 96 h / Ambient temperature

With lithium hydroxide; lithium aluminium tetrahydride; sodium cyanoborohydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm970161m

Reference yield:

methyl L-isoleucinate hydrochloride (18598-74-8) → (2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid (1026723-82-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / NaBH₃CN, AcOH / methanol

2: 74 percent / 1M aq. LiOH / dioxane / 96 h / Ambient temperature

With lithium hydroxide; sodium cyanoborohydride; acetic acid; In 1,4-dioxane; methanol;

DOI:10.1021/jm970161m

upstream raw materials:

(2S,3S)-2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentylamino)-3-methyl-pentanoic acid methyl ester

N-Cbz-L-Isoleucine

methyl L-isoleucinate hydrochloride

benzyl {(2S,3S)-1-[methoxy(methyl)amino]-3-methyl-1-oxopentan-2-yl}carbamate

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