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A Useful Condensation Activator Bearing Less Nucleophilicity and No Deliquescence
No.150(December 2012)
Wada et al. developed 1-(cyanomethyl)piperidinium tetrafluoroborate (1) conjugates, with a highly less nucleophilic counteranion, BF4-.1) It has appropriate proton-donating ability as a condensation activator to give the corresponding dinucleotide without any loss of the diastereopurity. In addition, the activator has no deliquescence and good solubility in CH3CN. Therefore, the activator can be broadly applicable to condensation reactions.
References
- 1)Synthesis of oligonucleoside phosphorothioates via the condensation reactions using 1-(cyanomethyl)piperidinium tetrafluoroborate
- a)N. Oka, T. Wada, K. Saigo, J. Am. Chem. Soc. 2002, 124, 4962.
- b)N. Oka, T. Wada, K. Saigo, J. Am. Chem. Soc. 2003, 125, 8307.
- c)S. Fujiwara, N. Iwamoto, K. Saigo, T. Sato, T. Wada, PCT Int. Appl. WO 2005092909.
- a)N. Oka, T. Wada, K. Saigo, J. Am. Chem. Soc. 2002, 124, 4962.
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