183051-99-2

Upstream product

• 100-52-7 benzaldehyde 
• 39798-19-1 Adenosine dialdehyde 
• 183051-95-8 9-((2R,4aR,6R,8aS)-8-Nitro-2-phenyl-4,4a,6,8a-tetrahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-9H-purin-6-ylamine 
• 2450-71-7 Propargylamine 
• 183051-90-3 (2R,4aR,6R,7S,8R,8aS)-6-(6-Amino-purin-9-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 
• 183051-91-4 (2R,4aR,6R,7R,8R,8aS)-6-(6-Amino-purin-9-yl)-8-nitro-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 

Relevant academic research and scientific papers

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

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.

Synthesis of Some New 3-Nitrohexopyranosyladenines and Related Compounds via Nitroolefin Intermediate as Potential Therapeutic Agents

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.