Starting from 3,4-di-O-acetyl-L-rhamnal (6) and thymine (7) the unsaturated nucleosides 1-(2′,3′,6′-trideoxy-4′-O-acetyl-α-and β-L-erythro-hex-2′-enopyranosyl)-thymine (8a and 8b) were prepared in anomerically pure form. In solution 8a was shown to be present in the 5Ho and oH5 conformations, whereas the predominant conformation of 8b was 5Ho. Chemical transformation of 8a and 8b led to the saturated nucleosides 1-(2′3′,6′-trideoxy-α-and β-L-eryrthro-hexopyranosyl)thymine (10a and 10b, respectively), which were converted into 1-(4′-azido-2′,3′,4′,6′-tetradeoxy-α-and β-L-threohexopyranosyl)thymine (12a and 12b). Preliminary biological studies showed that 9b was inactive against the HIV-1 and HIV-2 viruses.
ASJC Scopus subject areas
- Organic Chemistry