Nucleosides and nucleotides. LXVIII. A facile synthesis of 6,3'-methano-uridine and -cytidine from a 3-ketosugar.
- 1 January 1986
- journal article
- Published by Pharmaceutical Society of Japan in CHEMICAL & PHARMACEUTICAL BULLETIN
- Vol. 34 (1) , 423-425
- https://doi.org/10.1248/cpb.34.423
Abstract
The synthesis of 6, 3'-methanouridine was achieved by condensation of 2, 4-dimethoxy-6-lithiomethylpyrimidine with 5-O___--(tert-butyldi-methyl)silyl-1, 2-O___--isopropylidene-3-ketoxylose, followed by intramolecular glycosylation and deprotection. 6, 3'-Methanocytidine was also prepared from the 4-O___--methyl intermediate. The title compounds are the first example of uridine and cytidine fixed between C-6 and the 3'-position of pyrimidine nucleosides by a methylene group.Keywords
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