- Stereoselective synthesis of some 3-nitroglucopyranosyladenine analogues via a nitroolefin intermediate as potential therapeutic agents
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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.
- Tsuboike, Kazunari,Minamoto, Katsumaro,Mizuno, Gen,Yanagihara, Kazufomi
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p. 745 - 758
(2007/10/03)
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- Synthesis of Some New 3-Nitrohexopyranosyladenines and Related Compounds via Nitroolefin Intermediate as Potential Therapeutic Agents
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Synthesis of a series of 9-(4,6-O-benzylidene-3-nitro-β-D-hexopyranosyl)adenines (5, 6 and 7) was conducted.These were deprotected to the parent compounds 2, 3 and 4.The major glucopyranosyl isomer 6 with acetic anhydride-pyridine gave 9-(4,6-O-benzylidene-2,3-didehydro-2,3-dideoxy-3-nitro-β-D-hexapyranosyl)adenine (9), which was treated with morpholine, piperidine, allylamine, propargylamine, methyl glycinate, methanethiol sodium salt and thiophenol in the presence of KF to afford the corresponding 9-(3-nitro-2-(substituted)-β-D-glucopyranosyl)adenines (10a-10g).These were deprotected to the compounds 11a-11g.The olefin 9 with sodium borohydride gave the 2-deoxy analogue 12, which was deprotected to 13.Compound 10g with tributyltin hydride-AIBN yielded the 2,3-didehydro-2,3-dideoxy analogue 14.
- Tsuboike, Kazunari,Mizuno, Gen,Minamoto, Katsumaro
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p. S45 - S48
(2007/10/03)
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