Synthesis of Sugar Analogs Having a Phosphorus Atom in the Hemiacetal Ring (Phosphoro Sugar)

Abstract

Synthetic studies are reviewed on sugar analogs containing a phosphorus atom in the hemiacetal ring, e.g., analogs of D-xylo, D-gluco, 6-deoxy-L-galacto. D-mannopyranoses, as well as D-ribo and 2-deoxy-D-ribofu-ranoses. These compounds were converted into the corresponding per-O-acetyl derivatives, whose structures and conformations were established by ¹H-NMR spectral analyses and partly by X-ray crystallographic analyses. Stereoselectivity of the introduction of a phosphinyl group to various types of 6-O-tosyl-hex-5-uloses and 6-nitro-hex-5-enoses are also described.