321576-95-8

Upstream product

• 18162-48-6 tert-butyldimethylsilyl chloride 
• 196214-23-0 N-(3-hydroxypropyl)-2-nitrobenzenesulfonamide 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 162147-07-1 N,O-bis(tert-butyldimethylsilyl)-3-amino-1-propanol 
• 321576-93-6 N,O-bis(tert-butyldimethylsilyl)-N-o-nitrobenzenesulfonyl-3-amino-1-propanol 

Downstream Products

• 321576-97-0 (1S,2R,3S)-N-(3-tert-butyldimethylsilyloxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine 
• 321577-05-3 2-amino-5-[(1S,2R,3S)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylaminomethyl]-pyrrolo[2,3-d]pyrimidin-4(3H)-one 
• 321576-99-2 (1S,2R,3S)-N-(3-hydroxypropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine 
• 321577-03-1 N-(2-bromo-3-oxo-propyl)-N-(2,2-dimethyl-4,6a-dihydro-3aH-cyclopenta[1,3]dioxol-4-yl)-2-nitro-benzenesulfonamide 
• 321577-01-9 (1S,2R,3S)-N-(3-oxopropyl)-N-(o-nitrobenzenesulfonyl)-2,3-isopropylidinedioxycyclopent-4-enylamine 

Relevant academic research and scientific papers

Practical synthesis of spermine, thermospermine and norspermine

Polyamines, such as spermine (1), thermospermine (2) and norspermine (3), are widely distributed in nature, and have multiple biological activities. In addition, many of their conjugates have potential for pharmacological use. Here, we present a solid-phase synthesis using our nitrobenzenesulfonyl (Ns) strategy, which can provide 1, 2 and 3 on a gram scale. This approach should be suitable for facile construction of a diverse library of polyamines.

Total synthesis of Q base (Queuine)

The total synthesis of Q Base (Queuine) has been accomplished in eleven steps from ribose. Mitsunobu reaction of nosyl protected amine 12 with known cyclopentenol 7, derived from ribose, gave 13, the first key intermediate in the synthesis. The pyrrolo[2,3-d]pyrimidine ring system of Q Base was built via a cyclocondensation reaction between a β-aminobromoaldehyde 16, derived from the Mitsunobu product 13, and 2,4-diamino-6-hydroxypyrimidine. Deprotection of the product from the cycloccondensation reaction (17) gave Q Base. (C) 2000 Elsevier Science Ltd.