(3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

Base Information

• Chemical Name: (3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine
• CAS No.: 259657-20-0
• Molecular Formula: C₄₈H₆₂N₄O₁₀
• Molecular Weight: 855.041

Synonyms:(3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

Chemical Property of (3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

Chemical Property:

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Technology Process of (3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

There total 4 articles about (3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine 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: 64.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (R)-4-Ethylamino-1-[4-((R)-4-ethylamino-2-hydroxy-butylamino)-butylamino]-butan-2-ol (245107-51-1) → (3R,12R)-N1,N14-diethyl-3,12-dihydroxy-N1,N5,N10,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-20-0)

Guidance literature:

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

DOI:10.1021/jm990375z

Reference yield:

(3R,12R)-dibenzyloxy-N1,N14-diethyl-N1,N5,N10,N14-tetrakis(mesitylenesulfonyl)homospermine (259657-12-0) → (3R,12R)-N1,N14-diethyl-3,12-dihydroxy-N1,N5,N10,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-20-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / H₂; aq. AcOH / Pd / 20 °C / 760.05 Torr

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

3: 64 percent / aq. KHCO₃ / diethyl ether / 4 h / 20 °C

With hydrogen; sodium naphthalenide; potassium hydrogencarbonate; acetic acid; palladium; In 1,2-dimethoxyethane; diethyl ether; 1: debenzylation / 2: desulfonylation / 3: Condensation;

DOI:10.1021/jm990375z

Reference yield:

(2R)-2-(benzyloxy)-4-[N-(mesitylenesulfonyl)ethylamino]-O-tosyl-1-butanol (259657-11-9) → (3R,12R)-N1,N14-diethyl-3,12-dihydroxy-N1,N5,N10,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-20-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 50 percent / dimethylformamide / 16 h / 20 °C

2.1: 86 percent / H₂; aq. AcOH / Pd / 20 °C / 760.05 Torr

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

4.1: 64 percent / aq. KHCO₃ / diethyl ether / 4 h / 20 °C

With hydrogen; sodium naphthalenide; sodium hydride; potassium hydrogencarbonate; acetic acid; palladium; In 1,2-dimethoxyethane; diethyl ether; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Substitution / 2.1: debenzylation / 3.1: desulfonylation / 4.1: Condensation;

DOI:10.1021/jm990375z

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

(R)-4-Ethylamino-1-[4-((R)-4-ethylamino-2-hydroxy-butylamino)-butylamino]-butan-2-ol

(2R)-2-(benzyloxy)-4-[N-(mesitylenesulfonyl)ethylamino]-O-tosyl-1-butanol

(3R,12R)-N¹,N¹⁴-diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁰,N¹⁴-tetrakis(mesitylenesulfonyl)homospermine

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