(2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine

Base Information

• Chemical Name: (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine
• CAS No.: 202979-78-0
• Molecular Formula: C₃₁H₅₂N₄O₇
• Molecular Weight: 592.776

Synonyms:(2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine

Chemical Property of (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine

Chemical Property:

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Technology Process of (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine

There total 1 articles about (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N⁴,N⁸-bis(tert-butoxycarbonyl)spermidine 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: 72.0%

N1,N5-di-boc-spermidine (68076-39-1) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → (2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N4,N8-bis(tert-butoxycarbonyl)spermidine (202979-78-0)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at 0 ℃; for 21h;

DOI:10.7164/antibiotics.50.998

Reference yield: 18.0%

(2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N4,N8-bis(tert-butoxycarbonyl)spermidine (202979-78-0) → (2'S)-N4,N8-bis(tert-butoxycarbonyl)-N1-(N-(tert-butoxycarbonyl)-2-amino-3-phenylpropyl)spermidine (202979-79-1)

Guidance literature:

borane-THF; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.7164/antibiotics.50.998

Reference yield:

(2'S)-N-(tert-butoxycarbonyl)phenylalanyl-N4,N8-bis(tert-butoxycarbonyl)spermidine (202979-78-0) → (2'S)-N1-(2-amino-3-phenylpropyl)spermidine (202979-77-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 18 percent / BH₃*THF / tetrahydrofuran / 24 h / 20 °C

2: 79 percent / CF₃COOH / CH₂Cl₂ / 0.5 h / 20 °C

With trifluoroacetic acid; borane-THF; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: deprotection;

DOI:10.7164/antibiotics.50.998

upstream raw materials:

N₁,N₅-di-boc-spermidine

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

(2'S)-N⁴,N⁸-bis(tert-butoxycarbonyl)-N¹-(N-(tert-butoxycarbonyl)-2-amino-3-phenylpropyl)spermidine

(2'S)-N¹-(2-amino-3-phenylpropyl)spermidine

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