A new and efficient strategy for the synthesis of shimofuridin analogs: 2'-O-(4-O-stearoyl-alpha-L-fucopyranosyl)thymidine and -uridine.
Two shimofuridin analogs: 2'-O-(4-O-stearoyl-alpha-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-beta-D-ribofuranosyl)thymine (9) and -uracil (10) by coupling of 1,2-anhydro-3,5-di-O-benzyl-alpha-D-ribofuranose (8) with silylated thymine and uracil, and then stereoselective formation of the 1,2-cis (alpha) interglycoside bonds through condensation of the nucleoside derivatives 9 and 10 with 2-(2,3-di-O-benzyl-4-O-stearoyl-beta-L-fucopyranosylsulfonyl) pyrimidine (18). The 1,2-anhydro-3,5-di-O-benzyl-alpha-D-ribofuranose (8) was prepared by an improved procedure from D-arabinose.
Ning
Jun
J
Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences, PO Box 2871, Beijing 100085, PR China. fzkong@mil.rcees.ac.cn
Xing
Ying
Y
Kong
Fanzuo
F
D005663:Furans / Q000138:chemical synthesis; D007288:Inosine / Q000031:analogs & derivatives / Q000138:chemical synthesis; D009705:Nucleosides / Q000138:chemical synthesis*; D009904:Optical Rotation; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D014529:Uridine / Q000031:analogs & derivatives / Q000138:chemical synthesis*
C478184:2'-O-(4-O-stearoyl-alpha-L-fucopyranosyl)thymidine; C478183:2'-O-(4-O-stearoyl-alpha-L-fucopyranosyl)uridine; D005663:Furans; D009705:Nucleosides; C478182:shimofuridin A; D007288:Inosine; D013936:Thymidine; D014529:Uridine