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

Base Information

• Chemical Name: (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine benzyl ester
• CAS No.: 517877-34-8
• Molecular Formula: C₂₈H₃₂N₄O₇
• Molecular Weight: 536.585

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

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

Chemical Property:

Purity/Quality:

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

There total 3 articles about (S)-N-[(tert-butoxy)carbonyl]-γ-[N⁴-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine benzyl 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: 23.0%

N-benzyloxycarbonyl cytosine (149411-91-6) + 3-tert-butoxycarbonylamino-4-methanesulfonyloxy-butyric acid benzyl ester (149193-64-6) → (S)-N-[(tert-butoxy)carbonyl]-γ-[N4-(benzyloxycarbonyl)cytosin-1-yl]-β-homoalanine benzyl ester (517877-34-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 336h;

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 benzyl ester (517877-34-8)

Guidance literature:

Multi-step reaction with 3 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

With N-Ethylmaleimide; potassium carbonate; tert-butyl chloroformate; triethylamine; In tetrahydrofuran; 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 benzyl ester (517877-34-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Et₃N / tetrahydrofuran

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

With potassium carbonate; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

N-benzyloxycarbonyl cytosine

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

BOC-L-aspartic acid 4-benzyl ester

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

Downstream raw materials:

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

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