(S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine

Base Information

• Chemical Name: (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine
• CAS No.: 517877-35-9
• Molecular Formula: C₂₁H₂₆N₄O₇
• Molecular Weight: 446.46

Synonyms:(S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine

Chemical Property of (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine

There total 4 articles about (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine 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: 82.0%

(S)-N-[(tert-butoxy)carbonyl]-γ-[N4-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine benzyl ester (517877-34-8) → (S)-N-[(tert-butoxy)carbonyl]-γ-[N4-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine (517877-35-9)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 9h;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

Reference yield:

BOC-L-aspartic acid 4-benzyl ester (7536-58-5,98482-77-0) → (S)-N-[(tert-butoxy)carbonyl]-γ-[N4-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine (517877-35-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tBuOCOCl; NEM / tetrahydrofuran

1.2: 95 percent / NaBH₄ / methanol

2.1: 79 percent / Et₃N / tetrahydrofuran

3.1: 23 percent / K₂CO₃ / dimethylformamide / 336 h / 20 °C

4.1: 82 percent / aq. NaOH / dioxane / 9 h / 20 °C

With N-Ethylmaleimide; sodium hydroxide; potassium carbonate; tert-butyl chloroformate; triethylamine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

Reference yield:

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate (79069-16-2) → (S)-N-[(tert-butoxy)carbonyl]-γ-[N4-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine (517877-35-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 79 percent / Et₃N / tetrahydrofuran

2: 23 percent / K₂CO₃ / dimethylformamide / 336 h / 20 °C

3: 82 percent / aq. NaOH / dioxane / 9 h / 20 °C

With sodium hydroxide; potassium carbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(200211)85:11<3855::AID-HLCA3855>3.0.CO;2-A

upstream raw materials:

(S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine benzyl ester

BOC-L-aspartic acid 4-benzyl ester

benzyl (3S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxybutanoate

3-tert-butoxycarbonylamino-4-methanesulfonyloxy-butyric acid benzyl ester

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