Convenient syntheses of 7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2. 1]heptanes: α-L-ribo- and α-L-xylo-configured LNA nucleosides

Journal of Organic Chemistry

Volumn 65, Issue 17, 2000, Pages 5161-5166

  Håkansson, Anders E ^a   Koshkin, Alexei A ^b   Sørensen, Mads D ^a   Wengel, Jesper ^a,c  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b Exiqon AS   (Denmark)

^c UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; NUCLEIC ACID; NUCLEOSIDE;

ARTICLE; CHEMICAL STRUCTURE; ISOMER; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0037892646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo000232g     Document Type: Article

References (16)

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2. (b) Koshkin, A. A.; Singh, S. K.; Nielsen, P.; Rajwanshi, V. K.; Kumar, R.; Meldgaard, M.; Olsen, C. E.; Wengel, J. Tetrahedron 1998, 54, 3607.
3. Koshkin, A. A.; Nielsen, P.; Meldgaard, M.; Rajwanshi, V. K.; Singh, S. K.; Wengel, J. J. Am. Chem. Soc. 1998, 120, 13252.
4. We have defined LNA as an oligonucleotide containing one or more 2′-O,4′-C-methylene-β-D-ribofuranosyl nucleotide monomer(s). The natural β-D-ribo configuration is assigned to LNA (and LNA nucleosides) as the positioning of the 1-nitrogen and 2′-, 3′- and 5′-oxygen atoms follows that of RNA.
5. Obika, S.; Nanbu, D.; Hari, Y.; Andoh, J.; Mono, K.; Doi, T.; Imanishi, T. Tetrahedron Lett. 1998, 39, 5401.
6. (a) Rajwanshi, V. K.; Håkansson, A. E.; Dahl, B. M.; Wengel, J. Chem. Commun. 1999, 1395.
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9. Rajwanshi, V. K.; Kumar, R.; Hansen, M. K.; Wengel, J. J. Chem. Soc., Perkin Trans. 1 1999, 1407.
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14. Koshkin, A. A. Manuscript in preparation.
15. 4a
16. Nielsen, P.; Wengel, J. Chem. Commun. 1998, 2645.