Synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-13C]ribonucleosides.
The present efficient synthesis of [5'-13C]ribonucleosides and 2'-deoxy[5'-13C]ribonucleosides is characterized by the synthesis of the D-[5-13C]ribose derivative as an intermediate via the Wittig reaction of 4-aldehydo-D-erythrose dialkyl acetals with Ph3P13CH3I-BuLi to introduce the 13C label at the 5-position of a pentose. This was followed by the highly diastereoselective osmium dihydroxylation for the preparation of 2,3-di-O-benzyl-D-[5-13C]ribose dialkyl acetal and the cyclization from D-[5-13C]ribose dialkyl acetal derivatives to the alkyl D-[5-13C]ribofuranoside derivative by the use of LiBF(4). The obtained D-[5-13C]ribose derivative was converted into [5'-13C]ribonucleosides and subsequently into the corresponding 2'-deoxynucleosides.
Kawashima
Etsuko
E
Laboratory of Pharmaceutical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, Horinouchi, Hachioji, Tokyo, 192-0392 Japan. kawasima@ps.toyaku.ac.jp
Umabe
Kaoru
K
Sekine
Takeshi
T
D002247:Carbon Isotopes; D003853:Deoxyribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D002247:Carbon Isotopes; D003853:Deoxyribonucleosides; D012263:Ribonucleosides