title: Regioselective glycosylation: synthesis of alpha-indoline nucleosides.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, Ohio University, Athens, Ohio 45701, USA. brownk3@ohiou.edu
authors.forename: Kenneth L
authors.initials: KL
authors.lastname: Brown
authors.forename: Tilak
authors.initials: T
authors.lastname: Chandra
authors.forename: Shawn
authors.initials: S
authors.lastname: Zou
authors.forename: Edward J
authors.initials: EJ
authors.lastname: Valente
mesh_terms: D018360:Crystallography, X-Ray; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007211:Indoles; D012263:Ribonucleosides