(3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

Base Information

• Chemical Name: (3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine
• CAS No.: 259657-08-4
• Molecular Formula: C₄₈H₆₂N₄O₁₀
• Molecular Weight: 855.041

Synonyms:(3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

Chemical Property of (3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

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Technology Process of (3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,N¹⁴-tetrakis(benzyloxycarbonyl)homospermine

There total 4 articles about (3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxy-N¹,N⁵,N¹⁴,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: 83.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + (3S,12S)-N1,N14-Diethyl-3,12-dihydroxyhomospermine tetrahydrochloride (177798-02-6) → (3S,12S)-N1,N14-Diethyl-3,12-dihydroxy-N1,N5,N14,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-08-4)

Guidance literature:

With potassium hydrogencarbonate; In diethyl ether; at 20 ℃; for 5h;

DOI:10.1055/s-2001-14570

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) + ((S)-4-{4-[(S)-4-(Benzyloxycarbonyl-ethyl-amino)-2-hydroxy-butylamino]-butylamino}-3-hydroxy-butyl)-ethyl-carbamic acid benzyl ester (259657-06-2) → (3S,12S)-N1,N14-Diethyl-3,12-dihydroxy-N1,N5,N14,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-08-4)

Guidance literature:

With triethylamine; In chloroform; at 20 ℃; for 2h;

DOI:10.1021/jm990375z

Reference yield:

(3S,12S)-N5,N10-Dibenzyl-N1,N14-diethyl-3,12-dihydroxyhomospermine (361484-37-9) → (3S,12S)-N1,N14-Diethyl-3,12-dihydroxy-N1,N5,N14,N14-tetrakis(benzyloxycarbonyl)homospermine (259657-08-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / aq. HCl; H₂ / 10 percent Pd/C / ethanol / 5 h / 760 Torr

2: 83 percent / aq. KHCO₃ / diethyl ether / 5 h / 20 °C

With hydrogenchloride; hydrogen; potassium hydrogencarbonate; palladium on activated charcoal; In diethyl ether; ethanol;

DOI:10.1055/s-2001-14570

upstream raw materials:

benzyl chloroformate

((S)-4-{4-[(S)-4-(Benzyloxycarbonyl-ethyl-amino)-2-hydroxy-butylamino]-butylamino}-3-hydroxy-butyl)-ethyl-carbamic acid benzyl ester

N-(Benzyloxycarbonyloxy)succinimide

(3S,12S)-N¹,N¹⁴-Diethyl-3,12-dihydroxyhomospermine tetrahydrochloride

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