Chem. J. Chinese Universities ›› 2000, Vol. 21 ›› Issue (S1): 474.

• Synthetic Sciences • Previous Articles     Next Articles

Stereoselective Synthesis of α-Altropyranosyluridine Starting from Glucose

CHENG Chang-Mei1, HERDEWIJN Piet1, ZHAO Yu-Fen2   

  1. 1. Laboratory of Medicinal Chemistry, Rega Institute, Katholieke Universiteit Leuven, Minderbroedersstraat 10, B-3000 Leuven, Belgium;
    2. Bioorganic Phosphorus Chemistry Laboratory, Department of Chemistry, Tsinghua University, 100084 Beijing, China
  • Online:2000-12-31 Published:2000-12-31

Abstract:

α-Nucleoside is a kind of potential antiviral and antitumor agent, and of great interest in antisense and template directed reaction. β-Altropyranosyl-nucleosides have been synthesized and the properties of their oligo-nucleotides have been studied by Eshenmoser[1]. But it is very difficult to synthesize the α-anomer, because the direct coupling reaction leads to the β-anomer and the cyanamide route is not suitable due to the trans-configuration of 1,2-dihydroxyl groups in α-altrose. In order to resolve this problem, α-2, 1'-anhydroglucopyranosyluridine was synthesized by cyanamide route and it was hydrolyzed to title compound in good yield with 2',3'-configuration reversion.

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