Synthesis of bicyclo-DNA nucleosides with additional functionalization in the carbocyclic ring

Luisier, Samuel; Leumann, Christian J. (2008). Synthesis of bicyclo-DNA nucleosides with additional functionalization in the carbocyclic ring. CHIMIA, 62(4), pp. 270-272. Bern: Schweizerische Chemische Gesellschaft 10.2533/chimia.2008.270

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Two novel bicyclo nucleoside isomers carrying the base thymine in the furanose ring and an ester substituent in the carbocyclic ring were synthesized from a common bicyclic sugar precursor via a cyclopropanation/fragmentation pathway in nine steps. The relative configuration of the ester substituent in both isomers as well as the anomeric configuration in one nucleoside was determined by 1H-NMR difference NOE spectroscopy.

Item Type:

Journal Article (Original Article)

Division/Institute:

08 Faculty of Science > Departement of Chemistry and Biochemistry

UniBE Contributor:

Luisier, Samuel and Leumann, Christian

Subjects:

500 Science
500 Science > 540 Chemistry
500 Science > 570 Life sciences; biology

ISSN:

0009-4293

Publisher:

Schweizerische Chemische Gesellschaft

Language:

English

Submitter:

Christian Leumann

Date Deposited:

04 Oct 2013 15:11

Last Modified:

04 Feb 2016 08:59

Publisher DOI:

10.2533/chimia.2008.270

Web of Science ID:

000255973000019

BORIS DOI:

10.7892/boris.31037

URI:

https://boris.unibe.ch/id/eprint/31037 (FactScience: 195428)

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