Stereoselective synthesis of some 3-nitroglucopyranosyladenine analogues via a nitroolefin intermediate as potential therapeutic agents

Article abstract of DOI:10.1080/07328319808004672

Three isomers of 9-(4,6-O-benzylidene-3-deoxy-[β-D-hexopyranosyl) adenines (2-4) were isolated. The manno isomer 2 could be isomerized to the gluco isomer 3. The manno (2) and galacto isomer (4) were deprotected to 5 and 7, respectively. Michael addition of some organic amines and thiolates to the nitroolefin intermediate (8) gave the corresponding 2-(substituted)-3- nitro-glucopyranosides (9a-h). Compounds 9a,c,h were deprotected to 10a,c,h. Sodium azide with 8 gave the triazolo nucleoside 11, which was deprotected to 12.2-Deoxy-3-nitro analogue 14 was also obtained.

Full text of DOI:10.1080/07328319808004672

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Stereoselective Synthesis of Some 3-
Nitroglucopyranosyladenine Analogues
via a Nitroolefin: Intermediate as
Potential Therapeutic Agents
Kazunari TSUBOIKE a , Katsumaro MINAMOTO a , Gen MIZUNO a &
Kazufumi YANAGIHARA b
a Department of Applied Chemistry , Graduate School of Engineering,
Nagoya University , Furo-cho, Chikusa-ku, Nagoya, 464, Japan
b Synthesis Research Dept. , Central Research Institute , Nissan
Chemical Industries, Ltd., 722–1, Tsuboi-cho, Funabashi-shi, Chiba,
274, Japan
Published online: 13 Feb 2011.
To cite this article: Kazunari TSUBOIKE , Katsumaro MINAMOTO , Gen MIZUNO & Kazufumi
YANAGIHARA (1998) Stereoselective Synthesis of Some 3-Nitroglucopyranosyladenine Analogues via
a Nitroolefin: Intermediate as Potential Therapeutic Agents, Nucleosides and Nucleotides, 17:4,
745-758, DOI: 10.1080/07328319808004672
To link to this article: http://dx.doi.org/10.1080/07328319808004672
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