Collect. Czech. Chem. Commun. 2002, 67, 1681-1699

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


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.