An efficient alternative to DBU in the oxathiaphospholane (OTP) method for the solid phase synthesis of P-stereodefined phosphorothioate analogs

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Authors
Jastrzębska, Katarzyna ORCID logo 0000-0003-3979-3186
Date
2024-07-04
Journal Title
Journal ISSN
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Publisher
The Royal Society of Chemistry
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Abstract
This study presents a modified (extended) 1,3,2-oxathiaphospholane (OTP) method for the synthesis of P-stereodefined phosphorothioate analogs in the presence of previously unused organic bases. TBD (5,7-triazabicyclo[4.4.0]dec-5-ene) and Verkade's proazaphosphatrane (2,8,9-trimethyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane) are herein used for the first time as efficient organic bases compared to DBU, which is commonly used in the OTP approach. OTP method for the synthesis of P-stereodefined phosphorothioate has been extended to use activators TBD and Verkade base, which can be used interchangeably with DBU.
Description
This work was financially supported by National Centre of Science, Poland, grant UMO-2021/43/D/ST4/02433 (to K. J.). An Avance Neo 400 NMR spectrometer was purchased using funds provided by the EU Regional Operational Program of the Lodz Region RPLD.01.01.00-10-0008/18.
Keywords
stereocontrolled synthesis  stereoselective-synthesis  oligo(nucleoside phosphorothioate)s  dinucleotide phosphorothioates  thermal-stability  monomers  duplexes
Citation
Jastrzębska, K., (2024). An efficient alternative to DBU in the oxathiaphospholane (OTP) method for the solid phase synthesis of P-stereodefined phosphorothioate analogs. RSC ADVANCES. 14(20), 21174-21179. https://doi.org/10.1039/D4RA02833C
URI
https://open.icm.edu.pl/handle/123456789/25576
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