183051-99-2Relevant articles and documents
Stereoselective synthesis of some 3-nitroglucopyranosyladenine analogues via a nitroolefin intermediate as potential therapeutic agents
Tsuboike, Kazunari,Minamoto, Katsumaro,Mizuno, Gen,Yanagihara, Kazufomi
, p. 745 - 758 (2007/10/03)
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.