title: Stereocontrolled cyclization at the anomeric position of 6-(hydroxyalkyl)uridines using hypoiodite reaction.
abstract: Hypoiodite reaction of 6-(hydroxyalkyl)-2',3'-O-isopropylideneuridines (1-3) was found to yield a new class of spiro nucleosides having an anomeric orthoester structure. It appeared that the 6-hydroxyalkyl substituent and the 2',3'-O-isopropylidene group are working cooperatively to control the anomeric stereochemistry (beta/alpha = 35/1-2/1) of the cyclization.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
authors.forename: A
authors.initials: A
authors.lastname: Kittaka
authors.forename: H
authors.initials: H
authors.lastname: Tanaka
authors.forename: H
authors.initials: H
authors.lastname: Kato
authors.forename: T
authors.initials: T
authors.lastname: Asakura
authors.forename: K T
authors.initials: KT
authors.lastname: Nakamura
authors.forename: T
authors.initials: T
authors.lastname: Miyasaka
mesh_terms: D000478:Alkylation; D007202:Indicators and Reagents; D017613:Iodine Compounds; D015394:Molecular Structure; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D007202:Indicators and Reagents; D017613:Iodine Compounds; C081961:hypoiodous acid; D014529:Uridine