75306-67-1

Upstream product

• 13484-76-9 phenylformamidine 
• 62-53-3 aniline 
• 14152-97-7 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 
• 103-85-5 phenyl-carbamimidothioic acid 
• 142-04-1 aniline hydrochloride 
• 66118-22-7 (2R,3R,4S,5R,6R)-2-(acetoxymethyl)-6-isocyanotetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 121388-66-7 3-phenyl-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thiocarbamide 

Relevant academic research and scientific papers

Raney Nickel Desulphuration of 1-Substituted- and 1,3-Disubstituted-thioureas

Certain 1-aryl-1,3-diaryl- and 1-aryl-3-tetra-O-acetyl-β-D-glucopyranosyl thioureas have been successfully desulphurated into the related mono- and 1,3-di-substituted formamidines with the help of Raney nickel catalyst.A few of them have been converted into the corresponding formamides also.Structure of the products have been established through usual chemical transformations, ir, nmr and mass spectral analysis.

Reaction des glycosyl isonitriles avec les amines et les alcools

After complexation with metals, glycosylisonitriles 1 react with alcohols to give mainly orthoesters, if C-2 bears a participating group, and/or alkyl glycosides without particular stereoselectivity.In the case of amines, formamidines are obtained by α-addition to 1 in good yields.An example of further heterocyclisation is given with the stereospecific synthesis of the glucosylquinazolinone 15.

α-ADDITION DES AMINES SUR LES GLYCOSYL ISONITRILES

α-Addition reactions of glycosyl isonitriles with primary and secondary amines allowed to prepare substituted glycosyl formamidimes representing good precursors in the synthesis of nucleoides.