SYNTHESIS OF -2,3-DIDEOXY-BETA-D-RIBO-HEXOFURANOSYL)PYRIMIDINE, ,3-DIDEOXY-BETA-D-ERYTHRO-HEXOFURANOSYL)PYRIMIDINE AND DEOXY-BETA-D-ERYTHRO-HEX-2-ENOFURANOSYL)PYRIMIDINE NUCLEOSIDES
H. Hrebabecky et A. Holy, SYNTHESIS OF -2,3-DIDEOXY-BETA-D-RIBO-HEXOFURANOSYL)PYRIMIDINE, ,3-DIDEOXY-BETA-D-ERYTHRO-HEXOFURANOSYL)PYRIMIDINE AND DEOXY-BETA-D-ERYTHRO-HEX-2-ENOFURANOSYL)PYRIMIDINE NUCLEOSIDES, Collection of Czechoslovak Chemical Communications, 59(2), 1994, pp. 412-420
Azido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)uracil (XXII) and 3-dideox
y-beta-D-erythro-hex-2-enofuranosyl)uracil (VIII) were prepared starti
ng from l-3,5,6-tri-O-benzoyl-beta-D-glucofuranosyl)uracil (I) by a pr
ocedure described previously for thymine analogs. 1-(2,3-Dideoxy-beta-
D-erythro-hexofuranosyl)uracil (XIII) was obtained by catalytic hydrog
enation of 3-dideoxy-beta-D-erythro-hex-2-enofuranosyl)uracil (VII) an
d subsequent methanolysis. Reaction of dibenzoyl derivative VII, yl-2,
3-dideoxy-beta-D-erythro-hexofuranosyl)uracil (XII) and the diacetate
prepared by acetylation of azido derivative XXII with Lawesson's reage
nt, followed by methanolysis, afforded xy-beta-D-erythro-hex-2-enofura
nosyl)-4-thiouracil (X), i-deoxy-beta-D-erythro-hexofuranosyl)-4-thiou
racil (XV) and ,3-dideoxy-beta-D-ribo-hexofuranosyl)-4-thiouracil (XXI
II), respectively. Heating of thio derivatives X, XV and XXIII with me
thanolic ammonia at 100-degrees-C gave dideoxy-beta-D-erythro-hex-2-en
ofuranosyl)cytosine (XI), (2,3-dideoxy-beta-D-erythro-hexofuranosyl)cy
tosine (XVI) and ido-2,3-dideoxy-beta-D-ribo-hexofuranosyl)cytosine (X
XIV).