The Interaction of Per‐O‐Acetylated Acyclic 1‐(1‐Butylindol‐3‐yl)‐1‐deoxy‐ketoses with Silylated Uracil

Abstract

The per‐O‐acetylated open chain derivatives of 1‐(1‐butylindol‐3‐yl)‐1‐deoxy‐1‐L‐sorbose and 1‐(1‐butylindol‐3‐yl)‐1‐deoxy‐L‐tagatose, which are readily available by alkaline degradation of 1‐butylascorbigen followed by acetylation, were used in a nucleoside‐type synthesis. The interaction of these ketoses derivatives with bis‐(trimethylsilyl)‐uracil yielded in each case a mixture of (E)‐2,4,5,6‐tetra‐O‐acetyl‐1‐(1‐butylindol‐3‐yl)‐1,3‐dideoxy‐3‐(uracil‐1‐yl)‐L‐xylo‐hexa‐1‐enitol and (E)‐2,4,5,6‐tetra‐O‐acetyl‐1‐(1‐butylindol‐3‐yl)‐1,3‐dideoxy‐3‐(uracil‐1‐yl)‐L‐lyxo‐hexa‐1‐enitol, which were separated by preparative HPLC. The deacetylation of each of these compounds by MeONa in MeOH produced a mixture of 1‐(1‐butylindol‐3‐yl)‐1,3‐dideoxy‐4‐O‐methyl‐3‐(uracil‐1‐yl)‐α‐L‐sorbopyranose and 1‐(1‐butylindol‐3‐yl)‐1,3‐dideoxy‐4‐O‐methyl‐3‐(uracil‐1‐yl)‐β‐D‐fructopyranose, which were also separated by HPLC, the structures were confirmed by NMR.

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.

Keywords:

• 1‐Deoxy‐1‐(indol‐3‐yl)ketoses
• Uracil
• C‐ketosides

Acknowledgments

The work was supported by the Russian Foundation for Basic Research, project 03‐03‐32090. Authors thank Dr. Alexander M. Korolev for fruitful discussion.

Notes

^†In honor and celebration of the 70th birthday of Professor Leroy B. Townsend.