180404-49-3

Basic information

• Product Name: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-allofuranose
• Synonyms: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-allofuranose
• CAS NO: 180404-49-3
• Molecular Weight: 394.492
• Mol File: 180404-49-3.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-allofuranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-allofuranose(180404-49-3)
• EPA Substance Registry System: 3-deoxy-1,2:5,6-di-O-isopropylidene-3-(3-phenylthioureido)-α-D-allofuranose(180404-49-3)

Safety Data

• Hazardous Substances Data: 180404-49-3(Hazardous Substances Data)

Upstream product

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

Relevant articles and documents

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.

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