Abstract
The treatment of a piperidinium salt of 6-aryl-5-cyano-2-thiouracil with an O-peracetyl-α-D-pyranosyl bromide produces a mixture of N1-(β-D-pyranosyl)-2-thiouracil and its N1, S2-disubstituted analog. By contrast, the reaction of a silyl derivative of the 2-thiouracil with an O-peracetyl-β-D-pyranose furnishes the mononucleoside selectively. Both the mononucleoside/dinucleoside mixture and pure mononucleoside undergo ammonolysis under mild conditions to give the β-D-nucleoside of 6-aryl-5-cyano-2-thiocytosine. The silyl method also provides an easy access to β-D-ribosyl nucleosides.
Original language | English |
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Pages (from-to) | 8631-8636 |
Number of pages | 6 |
Journal | Tetrahedron |
Volume | 56 |
Issue number | 44 |
DOIs | |
Publication status | Published - Oct 27 2000 |
Keywords
- 1 -(β-D-furanosyl)-2-thiocytosines
- 1-(β-D-pyranosyl)-2-thiocytosines
- 6-aryl-5-cyano-2-thiouracils
- Ammonolysis
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry