3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I
- Author
- B Doboszewski, N Blaton, J Rozenski, André De Bruyn and Piet Herdewijn
- Organization
- Abstract
- A straightforward synthesis of 3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from beta-D-xylopyranosyl nucleosides. beta-D-xylopyranosyl thymine 17a,b,c and uracil 17d are converted into the 4'-benzoylated derivatives 18a,b and further into the 2',3'-enepyranosyl compounds 19b,c. A 3'-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a,b. Inversion of configuration of the 4'-position yielded the target nucleosides 22a,b. X-ray and H-1 NMR conformation analysis prove the equatorial orientation of the base moiety in the target compounds.
Downloads
-
(...).pdf
- full text (Published version)
- |
- UGent only
- |
- |
- 1.08 MB
Citation
Please use this url to cite or link to this publication: http://hdl.handle.net/1854/LU-193382
- MLA
- Doboszewski, B., et al. “3’-Deoxy-3’-Hydroxymethyl-Aldopentopyranosyl Nucleoside Synthesis. Part I.” TETRAHEDRON, vol. 51, no. 18, 1995, pp. 5381–96, doi:10.1016/0040-4020(95)00211-P.
- APA
- Doboszewski, B., Blaton, N., Rozenski, J., De Bruyn, A., & Herdewijn, P. (1995). 3’-deoxy-3’-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I. TETRAHEDRON, 51(18), 5381–5396. https://doi.org/10.1016/0040-4020(95)00211-P
- Chicago author-date
- Doboszewski, B, N Blaton, J Rozenski, André De Bruyn, and Piet Herdewijn. 1995. “3’-Deoxy-3’-Hydroxymethyl-Aldopentopyranosyl Nucleoside Synthesis. Part I.” TETRAHEDRON 51 (18): 5381–96. https://doi.org/10.1016/0040-4020(95)00211-P.
- Chicago author-date (all authors)
- Doboszewski, B, N Blaton, J Rozenski, André De Bruyn, and Piet Herdewijn. 1995. “3’-Deoxy-3’-Hydroxymethyl-Aldopentopyranosyl Nucleoside Synthesis. Part I.” TETRAHEDRON 51 (18): 5381–5396. doi:10.1016/0040-4020(95)00211-P.
- Vancouver
- 1.Doboszewski B, Blaton N, Rozenski J, De Bruyn A, Herdewijn P. 3’-deoxy-3’-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I. TETRAHEDRON. 1995;51(18):5381–96.
- IEEE
- [1]B. Doboszewski, N. Blaton, J. Rozenski, A. De Bruyn, and P. Herdewijn, “3’-deoxy-3’-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I,” TETRAHEDRON, vol. 51, no. 18, pp. 5381–5396, 1995.
@article{193382,
abstract = {{A straightforward synthesis of 3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleosides is described starting from beta-D-xylopyranosyl nucleosides. beta-D-xylopyranosyl thymine 17a,b,c and uracil 17d are converted into the 4'-benzoylated derivatives 18a,b and further into the 2',3'-enepyranosyl compounds 19b,c. A 3'-hydroxymethyl appendix has been introduced using a free-radical methodology to furnish 20a,b. Inversion of configuration of the 4'-position yielded the target nucleosides 22a,b. X-ray and H-1 NMR conformation analysis prove the equatorial orientation of the base moiety in the target compounds.}},
author = {{Doboszewski, B and Blaton, N and Rozenski, J and De Bruyn, André and Herdewijn, Piet}},
issn = {{0040-4020}},
journal = {{TETRAHEDRON}},
language = {{eng}},
number = {{18}},
pages = {{5381--5396}},
title = {{3'-deoxy-3'-hydroxymethyl-aldopentopyranosyl nucleoside synthesis. Part I}},
url = {{http://doi.org/10.1016/0040-4020(95)00211-P}},
volume = {{51}},
year = {{1995}},
}
- Altmetric
- View in Altmetric
- Web of Science
- Times cited: