Glycosylation of nucleoside bases with 2,3-dideoxy-1-thio-D-glycero-pento-2-enofuranosides.
Both intermolecular and intramolecular glycosylation of thymine using phenyl 2,3-dideoxy-1-thio-D-glycero-pent-2-enofuranoside as a glycosyl donor was investigated. When the reaction was carried out intermolecularly in the presence of NBS as the promoter, the corresponding 2',3'-unsaturated beta-nucleosides were obtained stereoselectively. On the other hand, the intramolecular glycosylation employing a 5-O-(2-pyrimidyl) derivative of similar thioglycoside afforded an unexpected product, in which thymine was incorporated at the C-3' position.
Sujino
K
K
Noguchi Institute, Tokyo, Japan.
Yoshida
T
T
Sugimura
H
H
D006031:Glycosylation; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry; D013941:Thymine / Q000138:chemical synthesis / Q000737:chemistry
D009705:Nucleosides; D013865:Thioglycosides; D013941:Thymine