Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles. Stairs, S. & Powner, M. W. Synlett, 28(19):2650–2654, 2017. doi abstract bibtex We report the efficient and scalable synthesis of 2,2′-anhydro-5-amino-1-$β$-arabinofuranosylimidazole-4-carboxamide and 2,2′-anhydro-5-amino-1-$β$-arabinofuranosylimidazole-4-carbonitrile from commercial arabino -adenosine. 2,2′-Anhydro-5-amino-1-$β$-arabinofuranosylimidazole-4-carboxamide is synthesised in only five steps with a single chromatographic purification. Additionally, we report a high-yielding, three-step conversion of 2,2′-anhydro-5-amino-1-$β$-arabinofuranosylimidazole-4-carboxamide into 2,2′-anhydro-5-amino-1-$β$-arabinofuranosylimidazole-4-carbonitrile. They are proposed key intermediates of the divergent prebiotic synthesis of ribonucleotides and this facile synthesis is anticipated to be instrumental in continued investigation of the origins of nucleotides.
@article{Stairs2017a,
abstract = {We report the efficient and scalable synthesis of 2,2′-anhydro-5-amino-1-$\beta$-arabinofuranosylimidazole-4-carboxamide and 2,2′-anhydro-5-amino-1-$\beta$-arabinofuranosylimidazole-4-carbonitrile from commercial arabino -adenosine. 2,2′-Anhydro-5-amino-1-$\beta$-arabinofuranosylimidazole-4-carboxamide is synthesised in only five steps with a single chromatographic purification. Additionally, we report a high-yielding, three-step conversion of 2,2′-anhydro-5-amino-1-$\beta$-arabinofuranosylimidazole-4-carboxamide into 2,2′-anhydro-5-amino-1-$\beta$-arabinofuranosylimidazole-4-carbonitrile. They are proposed key intermediates of the divergent prebiotic synthesis of ribonucleotides and this facile synthesis is anticipated to be instrumental in continued investigation of the origins of nucleotides.},
author = {Stairs, Shaun and Powner, Matthew W.},
doi = {10.1055/s-0036-1590968},
issn = {14372096},
journal = {Synlett},
keywords = {AICAR,arabinosides,nucleosides,prebiotic,purines},
number = {19},
pages = {2650--2654},
title = {{Scalable Synthesis of 2,2′-Anhydro-arabinofuranosyl Imidazoles}},
volume = {28},
year = {2017}
}
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