Convenient syntheses of 7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo

AE Hakansson; AA Koshkin; MD Sorensen; J Wengel

doi:10.1021/jo000232g

Convenient syntheses of 7-hydroxy-1-(hydroxymethyl)-3-(thymin-1-yl)-2,5-dioxabicyclo

J Org Chem. 2000 Aug 25;65(17):5161-6. doi: 10.1021/jo000232g.

Authors

AE Hakansson¹, AA Koshkin, MD Sorensen, J Wengel

Affiliation

¹ Department of Chemistry, University of Copenhagen, Denmark.

PMID: 10993341
DOI: 10.1021/jo000232g

Abstract

Synthesis of the diastereoisomeric LNA (locked nucleic acid) nucleosides 1-(2-O,4-C-methylene-alpha-L-ribofuranosyl)thymine (6) and 1-(2-O,4-C-methylene-alpha-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.