Synthesis of some novel 1-(5-thio-β-D-xylopyranosyl)-lumazine and -pyrimidine nucleosides

✍ Scribed by Najim A. Al-Masoudi; Wolfgang Pfleiderer

• Book ID: 104204417
• Publisher: Elsevier Science
• Year: 1993
• Tongue: French
• Weight: 713 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)87232-x

✦ Synopsis

1,2,3,4-Tetra-0-acetyl-5-thio-D-xylopyranose (1) reacts with the silylated lumazine bases (2-s) under trimgthylsilyl trifliioromethylsulfonate catalysis to give the nucleoSides f& 8, 10, and 12 respectively, which face deblocking with potassium carbonate iii dFy methanol to yield the free nucleosides & 2, 11, and 13 respectively. The synthesis of l-(2,3,4-tri-o-acetyl-5-thio-B-xyl@yranosyT)-thymine (17) and its free nucleoside 18 have been improved and in a similar manner reZ:ted the silylated pyrimidiic bases 15 and 16 to the 5-iodo-(19) and 5-fluoro-(21) analogues. Deacylation affordEd the free nucleosides-?P and ZE, respectively.