16434-48-3Relevant academic research and scientific papers
2′-C-alkylribonucleosides: Design, synthesis, and conformation
Harry-O'kuru, Rogers E.,Kryjak, Emily A.,Wolfe, Michael S.
, p. 1457 - 1460 (2007/10/03)
Certain 2′-C-alkylribonucleotides have been designed as potential mechanism-based inactivators of ribonucleotide reductases. A short, flexible route toward the corresponding nucleosides and NMR evidence concerning their preferred solution conformations are discussed. Copyright
A short, flexible route toward 2'-C-branched ribonucleosides
Harry-O'kuru,Smith,Wolfe
, p. 1754 - 1759 (2007/10/03)
A five-step synthesis of 2'-C-branched ribonucleosides from commercially obtained 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4) is described. The free hydroxyl group of 4 was oxidized in high yield with Dess-Martin periodane reagent. The resultant 2-ketosugar was treated with MeMgBr/TiCl4, CH2=CHMgBr/CeCl3, or TMSC≡CLi/CeCl3, and in each case addition to the ketone proceeded stereoselectively to provide 2-alkylated ribofuranosides. After conversion to the corresponding tetrabenzoyl derivatives, the 2-alkylribofuranosides were coupled to nucleobases under Vorbruggen persilylation conditions, giving the β-nucleosides with high stereoselectivity. Deprotection with methanolic ammonia provided the title compounds in 17-49% overall yields from 4.
A concise synthesis of 2'-C-methylribonucleosides
Wolfe,Harry-O'kuru
, p. 7611 - 7614 (2007/10/02)
2'-C-methylribonucleosides were synthesized in five steps from commercially available 1,3,5-tri-O-benzoyl-α-D-ribose with good overall yields.
