A new and efficient strategy for the synthesis of shimofuridin analogs: 2′-O-(4-O-stearoyl-α-l-fucopyranosyl)thymidine and -uridine Original Research Article

Two shimofuridin analogs: 2′-O-(4-O-stearoyl-α-l-fucopyranosyl)thymidine (2) and -uridine (3) have been synthesized using d-arabinose, l-fucose, thymine, uracil, and stearoyl chloride as the starting materials. The synthetic procedures involve the facile preparation of 1-(3,5-di-O-benzyl-β-d-ribofuranosyl)thymine (9) and -uracil (10) by coupling of 1,2-anhydro-3,5-di-O-benzyl-α-d-ribofuranose (8) with silylated thymine and uracil, and then stereoselective formation of the 1,2-cis (α) interglycoside bonds through condensation of the nucleoside derivatives 9 and 10 with 2-(2,3-di-O-benzyl-4-O-stearoyl-β-l-fucopyranosylsulfonyl) pyrimidine (18). The 1,2-anhydro-3,5-di-O-benzyl-α-d-ribofuranose (8) was prepared by an improved procedure from d-arabinose.