Pyrimidine nucleosides of the furanose form of 2-amino-2-deoxy-D-glucose

Abstract Partial demercaptalation of 2-deoxy-2-(trifluoroacetamido)- D -glucose diethyl dithioacetal yielded ethyl 2-deoxy-1-thio-2-(trifluoroacetamido)-α- D -glucofuranoside ( 2 ). This compound was also prepared by deacetylation of ethyl 2-acetamido-3,5,6-tri- O -acetyl-2-deoxy-1-thio-α- D -glucofuranoside followed by treatment of the product with S -ethyl trifluorothioacetate. Acetylation of 2 , followed by treatment with chlorine, gave 3,5,6-tri- O -acetyl-2-deoxy-2-(trifluoroacetamido)- D -glucofuranosyl chloride ( 6 ), which was condensed with bis(trimethylsilyl)cytosine to give 1-[3,5,6-tri- O -acetyl-2-deoxy-2-(trifluoroacetamido)-β- D -glucofuranosyl]cytosine ( 7 ). Compound 7 was deacylated with methanolic ammonia to give 1-(2-amino-2-deoxy-β- D -glucofuranosyl)cytosine, isolated as the sulfate. Condensation of 6 with bis(trimethylsilyl)-thymine yielded 1-[3,5,6-tri- O -acetyl-2-deoxy-2-(trifluoroacetamido)-β- D -glucofuranosyl]thymine, which was deacylated with methanolic ammonia to give 1-(2-amino-2-deoxy-β- D -glucofuranosyl)thymine, isolated as the hydrochloride.