N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE

Base Information

• Chemical Name: N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE
• CAS No.: 177213-61-5
• Molecular Formula: C20H42N4O4
• Molecular Weight: 402.578
• Hs Code.: 9999999999
• Mol file: 177213-61-5.mol

Synonyms:N2,N3-di-(tert-butyloxycarbonyl)-spermine;N4,N9-bis(tert-butyloxycarbonyl)-1,12-diamino-4,9-diazadodecane;(3-Amino-propyl)-{4-[(3-amino-propyl)-tert-butoxycarbonyl-amino]-butyl}-carbamic acid tert-butyl ester;N1,N4-di(tert-butyloxycarbonyl)-N1,N4-di(3-aminopropyl)-1,4-butanediamine;N4,N9-bis(tert-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane;N1,N4-di(tert-butoxycarbonyl)-N1,N4-di-(3-aminopropyl)-1.4-butanediamine;N(1),N(4)-di(tert-butyloxycarbonyl)-N(1),N(4)-di(3-aminopropyl)-1,4-butanediamine;

Chemical Property of N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE

Chemical Property:

• PSA: 111.12000
• LogP: 4.33900

Purity/Quality:

99% ^*data from raw suppliers

Spermine(HBBH) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: N4, N9-di-Boc-spermine is a spermine linker containing two a Boc-protected amino groups and two amine groups. The Boc groups can be deprotected under mild acidic conditions to form the free amine. The amino groups are reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. Spermidine is a polyamine that modulates various cellular activities like cellular development and differentiation, stability of DNA, and apoptosis.

Technology Process of N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE

There total 19 articles about N2,N3-BIS-(TERT-BUTYLOXYCARBONYL)-1,5,10,14-TETRA-AZA-QUATRODECANE 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: 100.0%

N4,N9-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile (194808-59-8) → di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate) (177213-61-5)

Guidance literature:

With lithium hydroxide monohydrate; palladium on activated charcoal; hydrogen; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1039/c0jm04064a

Reference yield: 100.0%

N1,N12-ditrifluoroacetyl-N4,N9-di(t-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane (193560-26-8) → di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate) (177213-61-5)

Guidance literature:

With ammonium hydroxide; In methanol; at 20 ℃; for 72h; pH=11;

DOI:10.1039/b105936j

Reference yield: 87.0%

Spermine (71-44-3) + di-tert-butyl dicarbonate (24424-99-5) → di-tert-butyl butane-1,4-diylbis((3-aminopropyl)carbamate) (177213-61-5)

Guidance literature:

Spermine; With ethyl trifluoroacetate,; In methanol; at 0 ℃; for 0.5h;

di-tert-butyl dicarbonate; In methanol; at 20 ℃;

With sodium hydroxide; In methanol; at 20 ℃; for 4h;

DOI:10.1021/jm049906w

upstream raw materials:

N₁,N₁₂-ditrifluoroacetyl-N₄,N₉-di(t-butoxycarbonyl)-1,12-diamino-4,9-diazadodecane

N⁴,N⁹-di(tert-butyloxycarbonyl)-3-(4-[(2-cyanoethyl)amino]butylamino)propanenitrile

[4-(tert-butoxycarbonyl-{3-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-propyl}-amino)-butyl]-{3-[1-(4,4-dimethyl-2,6-dioxo-cyclohexylidene)-ethylamino]-propyl}-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

C₄₀H₅₄Br₄N₄O₈

Refernces

• 1、 Ghonaim, Hassan M.,Li, Shi,Blagbrough, Ian S.. "N1,N12-diacyl spermines: SAR studies on non-viral lipopolyamine vectors for plasmid DNA and siRNA formulation". . p. 17 - 29. Retrieved 2010.
• 2、 Milelli, Andrea,Marchetti, Chiara,Greco, Maria Laura,Moraca, Federica,Costa, Giosuè,Turrini, Eleonora,Catanzaro, Elena,Betari, Nibal,Calcabrini, Cinzia,Sissi, Claudia,Alcaro, Stefano,Fimognari, Carmela,Tumiatti, Vincenzo,Minarini, Anna. "Naphthalene diimide-polyamine hybrids as antiproliferative agents: Focus on the architecture of the polyamine chains". . p. 107 - 122. Retrieved 2017/02/10.
• 3、 Feng, Xiangjun,Xia, Wenpin,Luo, Yu,Lu, Wei. "Mild and efficient synthesis of N1,N5,N 10-tri-tert-butoxycarbonyl spermine". . p. 274 - 278. Retrieved 2011/10/31.