Nucleosides. LIV. Synthesis and properties of 3'-azido- and 2',3'-dideoxy- 6,7-diphenyllumazine nucleosides

Article abstract of DOI:10.1080/15257779408013278

The best approach for the synthesis of 1-(3-azido-2,3-dideoxy-β-D- erythro-pentofuranosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7- diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy-β-D-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5'-position (17, 34, 49) followed by mesylation at the 3'-OH group and subsequent nucleophilic displacement by lithium azide afforded 19, 29 and 47 which were deprotected by acid treatment to give 3-5 in good yields. The syntheses of 1-(2,3-dideoxy-β-D-glycero- pentofuranosyl)- 6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-β-D-erythro-pentofuranosyl)- 6,7- diphenyllumazine and the corresponding 6,7-dimethyllumazine (26) via their 5'-O-p-toluoyl- (20, 30), and 3'-deoxy-3'-iodo derivatives (24, 31) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV- and NMR spectra.

Full text of DOI:10.1080/15257779408013278

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Nucleosides. LIV1 Synthesis and
Properties of 3′-Azido- and 2′,3′-
Dideoxy-6,7-diphenyllumazine
Nucleosides
Xiaodong Cao a & Wolfgang Pfleiderer a
a Fakultät für Chemie , Universität Konstanz , Postfach 5560,
D-78434, Konstanz, Germany
Published online: 23 Sep 2006.
To cite this article: Xiaodong Cao & Wolfgang Pfleiderer (1994) Nucleosides. LIV1 Synthesis and
Properties of 3′-Azido- and 2′,3′-Dideoxy-6,7-diphenyllumazine Nucleosides, Nucleosides and
Nucleotides, 13:1-3, 773-798, DOI: 10.1080/15257779408013278
To link to this article: http://dx.doi.org/10.1080/15257779408013278
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