By Maria N. Preobrazhenskaya, Ilya A. Korbukh (auth.), Leroy B. Townsend (eds.)
This 3rd of 4 volumes maintains the paintings of its well-received predecessors by means of supplying accomplished articles on particular traces of study. All volumes are written with medicinal chemists, natural chemists, actual chemists, and organic chemists in brain. also, with the spate of modern learn at the anticancer, antiviral, and antiparasitic houses of nucleosides and nucleotides, the volumes will curiosity oncologists, virologists, and pharmacologists.
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Extra resources for Chemistry of Nucleosides and Nucleotides: Volume 3
100) R' O~:' S;Me, - AoO R' l ___ 216a,b d"' :~ i O Hal ___ ~ AcO d"' :~ i a ~ HO OAc 217a,b OH 218a,b (a) R I =R 2 =H (b) R I = CH 3 • R2 = Ph By a similar method, 3-methyl-3-phenyl-l-p-n-ribofuranosylpyrrolidin-2,5-dione (218b) was obtained from 216b. (101) When 217a was dissolved in water-methanolic ammonia it produced the amide 219. The ring-opening reaction of 218b with Iysine yielded 220. (100) Ph r-+ ~O H 0 0 H NH, HO OH 219 CH 3 A .... - 0 ........... Ha ~ 1 HO NH-(CH2)4-CH-COOH ~H, OH 220 Another method for the synthesis of succinimide nucleosides is represented by a catalytic hydrogenation of isoshowdomycin (208, R = H) or its O-protected derivative 206 (R = H) to give the succinimide derivatives 210 or 209, respectively.
1 V-the half-wave potentials were measured on a Pt electrode). (64) For this reason, dehydrogenation of some l-glycosylnitroindolines with DDQ failed. y of DDQ, is the possibility of their use for dehydrogenation of O-unsubstituted l-glycosylindolines. Thus, 6-ni tro-l-p-o-ribofuranosylindoline, 6-thiocyano-l-a-L-arabinopyranosylindoline, and 6-fluoro-l-( 5-0-trityl-p-o-ribofuranosyl )indoline were converted to the corresponding indole nucleosides without preblocking of the hydroxy groups. Hydroquinones, which are formed in the course of dehydrogenation, exhibit acidic properties and cause side effects.
OH 1 Ind - CH - CH - CH20H Ind - CH - CH - CH20H 1 1 HO HO 241-threo 241-erythro Ind =O=J- Ind=O=J- 1 ~ ~ N 1 Ac OH R NH H h HOCH 1 HCOH 1 OH N H N H COR' C02Et R HO N H 1 H)(C=O 1, R 248 HCOH CH3 1 CH20H 249 HO 250 tives (257) which were cyclized to give 1,5,6,7-tetrahydro-2-(o-arabino-I,2,3,4-tetrahydroxybutyl)indol-4-ones (258). A similar reaction with l-amino-I-deoxy-o-fructose yielded the enamines 256, which were then converted into 258. (125,126) Usage of 2-benzylamino-2-deoxy-o-glycero-L-gluco-heptose and 5,5-dimethyl-I,3-cyclohexanedione in a similar reaction led to 2-o-lyxosyl-indol-4-one derivatives.