In:
Collection of Czechoslovak Chemical Communications, Institute of Organic Chemistry & Biochemistry, Vol. 71, No. 7 ( 2006), p. 956-977
Abstract:
The synthesis and properties of 7-deazapurine β-L-nucleosides are described. The stereoselective glycosylation of the anions of 2-amino-6-chloro-7-deazapurines 9a , 9b or 6-chloro-7-deazapurines 13a , 13d with 3,5-di- O -(4-methylbenzoyl)-2-deoxy-α-L- erythro -pentofuranosyl chloride ( 8 ) furnished the β-L-2'-deoxyribonucleosides 1 - 4 . The synthesis of β-L-ribonucleosides 5 - 7 used the Silyl-Hilbert-Johnson reaction (TMSOTf/BSA/MeCN) performed under Vorbrüggen conditions for the glycosylation of 7-halogenated 6-chloro-2-pivalamido-7-deazapurines 17b - 17d with 1- O -acetyl-2,3,5-tri- O -benzoyl-L-ribofuranose ( 16 ). Single-crystal X-ray analyses were performed and CD spectra were measured to assign the configuration. The antiviral activity against selected DNA and RNA viruses is reported.
Type of Medium:
Online Resource
ISSN:
0010-0765
,
1212-6950
DOI:
10.1135/cccc20060956
Language:
English
Publisher:
Institute of Organic Chemistry & Biochemistry
Publication Date:
2006
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