240423-19-2

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 240423-12-5 11-tert-butoxycarbonylamino-4,8-bis(2-nitrobenzenesulfonyl)-4,8-diazaundecan-1-ol 
• 196214-23-0 N-(3-hydroxypropyl)-2-nitrobenzenesulfonamide 
• 240423-18-1 N-(tert-butoxycarbonyl)-N'-(2-nitrobenzenesulfonyl)-1,3-propanediamine 
• 240423-11-4 7-tert-butoxycarbonylamino-4-(2-nitrobenzenesulfonyl)-4-azaheptan-1-yl bromide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 240423-09-0 N-(6-aminopropyl)-2-nitrobenzenesulfonamide 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 

Downstream Products

• 240423-15-8 N-[16-tert-butoxycarbonylamino-5,9,13-tris(2-nitrobenzenesulfonyl)-5,9,13-triazahexadecan-1-yl]-1H-indole-3-acetamide 
• 240423-16-9 N-[16-amino-5,9,13-tris(2-nitrobenzenesulfonyl)-5,9,13-triazahexadecan-1-yl]-1H-indole-3-acetamide 
• 133823-88-8 HO 416b 
• 240423-13-6 11-tert-butoxycarbonylamino-4,8-bis(2-nitrobenzenesulfonyl)-4,8-diazaundecan-1-yl iodide 

Relevant academic research and scientific papers

Total synthesis of polyamine toxin HO-416b and Agel-489 using a 2-nitrobenzenesulfonamide strategy

Total synthesis of spider toxins HO-416b (1) and Agel-489 (2) was accomplished using the 2-nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. In this strategy, the C-N bonds were constructed by alkylation of sulfonamides with alkyl halides or Mitsunobu reaction with the corresponding alcohol. Beginning with monoprotection of the symmetrical diamine, the construction of the backbone from diamine 3 was efficiently accomplished in 7 steps for 14 and 9 steps for 29. Removal of the Ns group while the substrate was attached to a novel solid support enabled the efficient isolation of this highly polar compound.

Total synthesis of polyamine toxin HO-416b utilizing the 2- nitrobenzenesulfonamide protecting group

The total synthesis of HO-416b (1) was accomplished using the 2- nitrobenzenesulfonamide (Ns) group as both a protecting and activating group. Starting with monosulfonylated diamines 2 and 3, three C-N bonds were constructed via alkylation of sulfonamides with alkyl halides. Removal of the Ns groups while the substrate was attached to a novel solid support enabled the efficient isolation of pure 1.