Convenient Syntheses of 7-Hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptanes: α-L-Ribo- and α-L-Xylo-Configured LNA Nucleosides

Article abstract of DOI:10.1021/jo000232g

Synthesis of the diastereoisomeric LNA (locked nucleic acid) nucleosides 1-(2-O,4-C-methylene-α-L-ribofuranosyl)thymine (6) and 1-(2-O,4-C-methylene-α-L-xylofuranosyl)thymine (13) are reported via convenient reaction cascades from di-O-p-toluenesulfonyl and tri-O-methanesulfonyl nucleoside derivatives 3, 7, and 10.