N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester
• CAS No.: 104754-56-5
• Molecular Formula: C₂₄H₂₂N₂O₈
• Molecular Weight: 466.447

Synonyms:N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester

Chemical Property of N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester

Chemical Property:

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Technology Process of N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester

There total 5 articles about N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)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: 69.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamate (104754-53-2) → N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester (104754-56-5)

Guidance literature:

With dicyclohexyl-carbodiimide; In tetrahydrofuran; for 0.25h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

α-ketoglutaric acid (328-50-7) → N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester (104754-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / 4 h / 80 °C / 10 - 15 Torr

2: 84 percent / Et₃N / dimethylformamide / 2 h / 90 °C

3: 98 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C

4: 69 percent / N,N-dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 0.25 h / Ambient temperature

With triethylamine; dicyclohexyl-carbodiimide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96774-2

Reference yield:

O-benzyl carbamate (621-84-1) → N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamic-γ-(N-hydroxysuccinimide)ester (104754-56-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / 4 h / 80 °C / 10 - 15 Torr

2: 84 percent / Et₃N / dimethylformamide / 2 h / 90 °C

3: 98 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene (DBU) / tetrahydrofuran / 0.5 h / 0 °C

4: 69 percent / N,N-dicyclohexylcarbodiimide (DCC) / tetrahydrofuran / 0.25 h / Ambient temperature

With triethylamine; dicyclohexyl-carbodiimide; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96774-2

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

N-benzyloxycarbonyl-α-benzyl-(Z)-α,β-dehydroglutamate

α-ketoglutaric acid

O-benzyl carbamate

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