177906-37-5

Basic information

• Product Name: (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester
• Synonyms: (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester
• CAS NO: 177906-37-5
• Molecular Weight: 834.973
• Mol File: 177906-37-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester(177906-37-5)
• EPA Substance Registry System: (3-Azido-propyl)-[2-(5-{(S)-2-[2-(2,4-bis-benzyloxy-phenyl)-acetylamino]-3-carbamoyl-propionylamino}-pentylcarbamoyl)-ethyl]-carbamic acid benzyl ester(177906-37-5)

Safety Data

• Hazardous Substances Data: 177906-37-5(Hazardous Substances Data)

Upstream product

• 113978-98-6 dibenzyl-2,4-dihydroxyphenylacetic acid N-hydroxysuccinimide ester 
• 177906-34-2 {2-[5-((S)-2-Amino-3-carbamoyl-propionylamino)-pentylcarbamoyl]-ethyl}-(3-azido-propyl)-carbamic acid benzyl ester 
• 100-39-0 benzyl bromide 
• 177906-33-1 [(S)-1-(5-{3-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-propionylamino}-pentylcarbamoyl)-2-carbamoyl-ethyl]-carbamic acid tert-butyl ester 
• 177906-28-4 3-[Benzyloxycarbonyl-(3-methanesulfonyloxy-propyl)-amino]-propionic acid methyl ester 
• 177906-30-8 3-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-propionic acid 
• 10494-79-8 methyl N-(3-hydroxypropyl)-β-alaninate 
• 22877-01-6 2,4-bis(benzyloxy)acetophenone 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 177906-31-9 3-[(3-Azido-propyl)-benzyloxycarbonyl-amino]-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 177906-29-5 methyl 7-azido-4-benzyloxycarbonyl-4-azaheptanoate 
• 177906-27-3 methyl 4-benzyloxycarbonyl-7-hydroxy-4-azaheptanoate 
• 177906-32-0 N-[N^α-(tert-butoxycarbonyl)-L-asparaginyl]-1,5-diaminopentane 
• 151255-80-0 2,4-dibenzyloxyphenylacetic acid methyl ester 

Relevant articles and documents

Total syntheses of spidamine and joramine, polyamine toxins from the joro spider, Nephila clavata

In order to confirm the structures of spidamine and joramine, identified from the venom of a spider (nephila clavata), we convergently synthesized both compounds, which have a common side chain of N-(L-asparaginyl)-N'-(3- aminopropyl-β-alanyl)-1,5-pentanediamine. A synthon of the common side chain was synthesized by starting with n-propanolamine which was converted to 7- azido-N-benzyloxycarbonyl-4-azaheptanoic acid N-hydroxysuccinimidyl ester. The ester was coupled with tert-butyloxycarbonyl-L-asparaginyl-1,5- pentanediamine to give the synthon of the common side chain. In the final synthesis of spidamine, the synthon of the common side chain was reacted with 2,4-dibenzyloxyphenylacetic acid N-hydroxysuccinimidyl ester, obtained by Willgerodt-kindler reaction of 2,4-dihydroxyacetophenone. The protected spidamine was catalytically hydrogenated to remove protective groups, affording spidamine itself in 13% yield from n-propanolamine. In the final synthesis of joramine, the synthon of the common side chain was reacted with 4-benzyloxyphenyl acetic acid N-hydroxysuccinimidyl ester. The protected joramine was also catalytically hydrogenated to produce joramine itself in 11% yield. The conformations of both synthesized compounds were analyzed by 1H-NMR and 13C-NMR. Their blocking activities on glutamate receptors were examined using lobster neuromuscular synapses.