Regioselective glycosylation: synthesis of alpha-indoline nucleosides.

Nucleosides Nucleotides Nucleic Acids

Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA.

Published: December 2005

Novel indoline ribonucleosides with the alpha-N-glycoside configuration are synthesized with very high regioselectivity in 90-96%yield, using TMS protected indolines and 2,3-O-(1-methylethylidene)-5-O-(triphenylmethyl)-alpha/beta-D-ribofuranose. The structures of these ribonucleosides were elucidated with X-ray crystallography as well as 2D (NOESY, COSY, and HMQC) NMR spectroscopy.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1383618PMC
http://dx.doi.org/10.1081/NCN-200067398DOI Listing

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