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Synthesis and Conformational Analysis of 1′‐ and 3′‐Substituted 2‐Deoxy‐2‐fluoro‐D‐ribofuranosyl Nucleosides by Grigorii G. Sivets; Elena N. Kalinichenko; Igor A. Mikhailopulo is a Chemistry article available to read on EtoBox.

What is Synthesis and Conformational Analysis of 1′‐ and 3′‐Substituted 2‐Deoxy‐2‐fluoro‐D‐ribofuranosyl Nucleosides about?

## Abstract Convergent syntheses of the 9‐(3‐X‐2,3‐dideoxy‐2‐fluoro‐__β__‐D‐ribofuranosyl)adenines **5** (X=N~3~) and **7** (X=NH~2~), as well as of their respective __α__‐anomers **6** and **8**, are described, using methyl 2‐azido‐5‐__O__‐benzoyl‐2,3‐dideoxy‐2‐fluoro‐__β__‐D‐ribofuranoside (**4**) as glycosylating agent. Methyl 5‐__O__‐benzoyl‐2,3‐dideoxy‐2,3‐difluoro‐__β__‐D‐ribofuranoside (**12**) was prepared starting from two precursors, and coupled with silylated __N__^6^‐benzoyladenine to afford, after deprotection, 2′,3′‐dideoxy‐2′,3′‐difluoroadenosine (**13**). Condensation of 1‐__O__‐acetyl‐3,5‐di‐__O__‐benzoyl‐2‐deoxy‐2‐fluoro‐__β__‐D‐ribofuranose (**14**) with silylated __N__^2^‐palmitoylguanine gave, after chromatographic separation and deacylation, the __N__^7^‐__β__‐anomer **17** as the main product, along with 2′‐deoxy‐2′‐fluoroguanosine (**15**) and its __N__^9^‐__α__‐anomer **16** in a ratio of __ca.__ 42 : 24 : 10. An in‐depth conformational analysis of a number of 2,3‐dideoxy‐2‐fluoro‐3‐X‐D‐ribofuranosides (X=F, N~3~, NH~2~, H) as well as of purine and pyrimidine 2‐deoxy‐2‐fluoro‐D‐ribofuranosyl nucleosides was performed using the PSEUROT (version 6.3) software

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Author

Grigorii G. Sivets; Elena N. Kalinichenko; Igor A. Mikhailopulo

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

2007

Language

EN

Field

Chemistry (Physical Sciences)