218915-29-8

Upstream product

• 180404-53-9 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-glucofuranose 
• 16848-19-4 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 103-72-0 phenyl isothiocyanate 

Relevant academic research and scientific papers

Synthesis and stereoelectronic properties of sugar-shaped polyhydroxylated hexahydropyrimidine-2-thiones

The reactivity and conformations in water solution of polyhydroxylated hexahydropyrimidine-2-thiones structurally related to biologically active nonulosonic acids and azaoctitols, obtained by intramolecular cyclization of sugar-derived μ-oxothioureas, have been investigated. The total preference for the axial orientation of the pseudoanomeric C - O bond and the high tendency to undergo acid-promoted intramolecular glycosylation are interpreted in terms of stabilizing hyperconjugative interactions in both the aminoketalic derivatives and the reactive azacarbenium cations. Moreover, repulsion between lone pairs and vicinal C - H bonds leads to a preference for structures bearing axial α-carbon substituents. The present results provide strong experimental evidence for the predominance of molecular orbital over electrostatic interactions in the stereoelectronic properties of these systems.