Stereocontrolled cyclization at the anomeric position of 6-(hydroxyalkyl)uridines using hypoiodite reaction.
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.
Kittaka
A
A
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Tanaka
H
H
Kato
H
H
Asakura
T
T
Nakamura
K T
KT
Miyasaka
T
T
D000478:Alkylation; D007202:Indicators and Reagents; D017613:Iodine Compounds; D015394:Molecular Structure; D013237:Stereoisomerism; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry
D007202:Indicators and Reagents; D017613:Iodine Compounds; C081961:hypoiodous acid; D014529:Uridine