Simple and efficient solution-phase synthesis of oligonucleotides using extractive work-up

Organic Process Research and Development

Volumn 10, Issue 6, 2006, Pages 1238-1245

  De Koning, Martijn C ^a   Ghisaidoobe, Amar B T ^a   Duynstee, Howard I ^b   Ten Kortenaar, Paul B W ^b   Filippov, Dmitri V ^a   Van Der Marel, Gijs A ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b Diosynth BV   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845507546     PISSN: 10836160     EISSN: None     Source Type: Journal    
DOI: 10.1021/op060133q     Document Type: Article

References (18)

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10. (a) Dueymes, C.; Schönberger, A.; Adamo, I.; Navarro, A. E.; Meyer, A.; Lange, M.; Imbach, J. L.; Link, F.; Morvan, F.; Vasseur, J. J. Org. Lett. 2005, 7, 3485.
11. (b) Adamo, I.; Dueymes, C.; Schönberger, A.; Navarro, A. E; Meyer, A.; Lange, M.; Imbach, J. L; Link, F.; Morvan, F.; Vasseur, J. J. Eur. J. Org. Chem. 2006, 436.
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14. It appears that the size and composition of the oligonucleotide influences the acidity of the reaction mixture. Byproducts originating from depurination in 8 and 9 were not detected by LC-MS analysis.
15. It is of interest to note that the EtOAc/THF organic phase posesses improved solubilizing power for ONs compared to EtOAc.
16. Yields were estimated by comparison of the obtained and the expected amounts of material (in mg).
17. Reaction time of 48 h was necessary for complete removal of the adamantylacetyl moiety.
18. -1.