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

Add time:08/15/2019    Source:sciencedirect.com

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.

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