180404-53-9

Upstream product

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

Downstream Products

• 218915-29-8 3-amino-3-deoxy-N-phenyl-β-D-glucofuranosylamine 1,3-(cyclic thiourea) 

Relevant academic research and scientific papers

Influence of intramolecular hydrogen-bonding on the conformation of 3-deoxy-3-thioureido sugars

3-Deoxy-3-thioureido derivatives of 1,2:5,6-di-O-isopropylidene-α-D-allofuranose and 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose were prepared, and their conformational properties in chloroform-d solutions were studied by temperature variable 1H NMR spe

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.

Tautomeric rearrangement of 3-deoxy-3-thioureidoaldoses: a novel synthetic route to carbohydrate mimics having a cyclic thiourea structure

Cyclic thiourea glycomimetics structurally realted to 3-deoxy-2-nonulosonic acids (KDNs) and 1,5-dideoxy-1,5-iminooctitols (azaoctitols) have been prepared by tautomeric rearrangement of 3-deoxy-3-thioureidoaldohexoses; the conformational properties of these compounds are governed by stereoelectronic requirements, mainly the anomeric effect.