(2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine

Base Information

• Chemical Name: (2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine
• CAS No.: 259656-94-5
• Molecular Formula: C₄₅H₅₆N₄O₁₀
• Molecular Weight: 812.96

Synonyms:(2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine

Chemical Property of (2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine

Chemical Property:

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Technology Process of (2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine

There total 3 articles about (2R,10R)-N¹,N¹¹-diethyl-2,10-dihydroxy-N¹,N⁴,N⁸,N¹¹-tetrakis(benzyloxycarbonyl)norspermine 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: 54.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (2R,10R)-N1,N11-diethyl-2,10-dihydroxynorspermine tetrahydrochloride → (2R,10R)-N1,N11-diethyl-2,10-dihydroxy-N1,N4,N8,N11-tetrakis(benzyloxycarbonyl)norspermine (259656-94-5)

Guidance literature:

With potassium hydrogencarbonate; In diethyl ether; at 20 ℃; for 4h;

DOI:10.1021/jm990375z

Reference yield:

(2R,10R)-N4,N8-dibenzyl-2,10-dihydroxynorspermine (259656-78-5) → (2R,10R)-N1,N11-diethyl-2,10-dihydroxy-N1,N4,N8,N11-tetrakis(benzyloxycarbonyl)norspermine (259656-94-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / H₂; 1 N HCl / 10percent Pd/C / ethanol / 22 h / 760.05 Torr

2: 54 percent / aq. KHCO₃ / diethyl ether / 4 h / 20 °C

With hydrogenchloride; hydrogen; potassium hydrogencarbonate; 10percent Pd/C; In diethyl ether; ethanol; 1: debenzylation / 2: Condensation;

DOI:10.1021/jm990375z

Reference yield:

(2S,10S)-N1,N11-bis(p-toluenesulfonyl)-N4,N8-dibenzyl-N1,N11-diethyl-2,10-dihydroxynorspermine (259656-76-3) → (2R,10R)-N1,N11-diethyl-2,10-dihydroxy-N1,N4,N8,N11-tetrakis(benzyloxycarbonyl)norspermine (259656-94-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 50 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / -78 °C

2: 82 percent / H₂; 1 N HCl / 10percent Pd/C / ethanol / 22 h / 760.05 Torr

3: 54 percent / aq. KHCO₃ / diethyl ether / 4 h / 20 °C

With hydrogenchloride; hydrogen; sodium naphthalenide; potassium hydrogencarbonate; 10percent Pd/C; In 1,2-dimethoxyethane; diethyl ether; ethanol; 1: detosylation / 2: debenzylation / 3: Condensation;

DOI:10.1021/jm990375z

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

(2R,10R)-N⁴,N⁸-dibenzyl-2,10-dihydroxynorspermine

(2S,10S)-N¹,N¹¹-bis(p-toluenesulfonyl)-N⁴,N⁸-dibenzyl-N¹,N¹¹-diethyl-2,10-dihydroxynorspermine

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