benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate

Base Information

• Chemical Name: benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate
• CAS No.: 647848-02-0
• Molecular Formula: C₃₂H₃₆N₂O₇
• Molecular Weight: 560.647

Synonyms:benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate

Chemical Property of benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate

Chemical Property:

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Technology Process of benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate

There total 6 articles about benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-tert-butyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate 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: 84.0%

di-tert-butyl dicarbonate (24424-99-5) + benzyl Nα-fluorenylmethyloxycarbonyl-Nγ-methoxy-α,γ-diamino-L-butanoate (647848-00-8) → benzyl Nα-fluorenylmethyloxycarbonyl-Nγ-tert-butyloxycarbonyl-Nγ-methoxy-α,γ-diamino-L-butanoate (647848-02-0)

Guidance literature:

In tetrahydrofuran; at 45 ℃;

DOI:10.1039/b306142f

Reference yield:

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → benzyl Nα-fluorenylmethyloxycarbonyl-Nγ-tert-butyloxycarbonyl-Nγ-methoxy-α,γ-diamino-L-butanoate (647848-02-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 85 percent / aq. NaHCO₃ / acetonitrile

2.1: Cs₂CO₃ / dimethylformamide

2.2: 48 percent / dimethylformamide / 6 h

3.1: 63 percent / DMSO; oxalyl chloride; N,N-diisopropylethylamine / CH₂Cl₂ / -60 - 0 °C

4.1: 95 percent / 4 Angstroem molecular sieves / pyridine

5.1: 99 percent / NaBH₃CN / acetic acid / 3 h

6.1: 84 percent / tetrahydrofuran / 45 °C

With oxalyl dichloride; 4 A molecular sieve; sodium cyanoborohydride; sodium hydrogencarbonate; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile; 3.1: Swern oxidation;

DOI:10.1039/b306142f

Reference yield:

Nα-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine (172525-85-8) → benzyl Nα-fluorenylmethyloxycarbonyl-Nγ-tert-butyloxycarbonyl-Nγ-methoxy-α,γ-diamino-L-butanoate (647848-02-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: Cs₂CO₃ / dimethylformamide

1.2: 48 percent / dimethylformamide / 6 h

2.1: 63 percent / DMSO; oxalyl chloride; N,N-diisopropylethylamine / CH₂Cl₂ / -60 - 0 °C

3.1: 95 percent / 4 Angstroem molecular sieves / pyridine

4.1: 99 percent / NaBH₃CN / acetic acid / 3 h

5.1: 84 percent / tetrahydrofuran / 45 °C

With oxalyl dichloride; 4 A molecular sieve; sodium cyanoborohydride; caesium carbonate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; acetic acid; N,N-dimethyl-formamide; 2.1: Swern oxidation;

DOI:10.1039/b306142f

upstream raw materials:

di-tert-butyl dicarbonate

benzyl N^α-fluorenylmethyloxycarbonyl-N^γ-methoxy-α,γ-diamino-L-butanoate

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

N^α-(Fluoren-9-ylmethoxycarbonyl)-L-homoserine

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