Collect. Czech. Chem. Commun.
2002, 67, 1681-1699
https://doi.org/10.1135/cccc20021681
Synthesis of Racemic 2-Hydroxy-4- and 2-Hydroxy-5-(hydroxymethyl)cyclohexane Nucleoside Analogues
Hubert Hřebabecký*, Milena Masojídková and Antonín Holý
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 166 10 Prague 6, Czech Republic
Abstract
New racemic 2-hydroxy-4- and 2-hydroxy-5-(hydroxymethyl)cyclohexane analogues of adenine (10b and 16b) and thymine nucleosides (13b and 19b) were prepared by alkylation of 1,8-diazabicyclo[5.4.0]undec-7-ene salt of adenine and/or thymine with 3-vinyl-7-oxabicyclo[4.1.0]heptane followed by cis hydroxylation with osmium(VIII) oxide and sodium chlorate, oxidation with sodium periodate, and borohydride reduction.
Keywords: Carbanucleosides; Carbocyclic nucleosides; Nucleosides; Cyclohexanes; Adenine; Thymine; Antivirals; Epoxides; NMR spectroscopy.
References: 31 live references.
