Synthesis of 3'-amino-2',3'-dideoxy-hexofuranose nucleosides with potential anti-viral activity.
Michael type addition of DBU (1,8-diazabicyclo[5,4,0]undec-7-ene) phthalimide salt to 4,6-di-O-acetyl-2,3-dideoxy-aldehydo-D-erythro-trans-hex-2-enos e 2 and concomitant acetyl shift give an anomeric mixture of arabino and ribo isomers of 5,6-di-O-acetyl-2,3-dideoxy-3-phthalimido-D-hexofuranose 3 which after acetylation at the anomeric hydroxy group is separated to give 4 and 5. Subsequent reaction with 5'-substituted silylated uracil in the presence of TMS-triflate results in three different 5',6'-di-O-acetyl-2',3'-dideoxy-3'-phthalimido-D-hexofuranose nucleosides 7, 9, and 10 which were deprotected to give the corresponding 3'-amino nucleosides 8, 11, and 12. The compounds 7-12 were investigated for their activity against HSV-1 and HIV-1.
Lau
J
J
Department of Chemistry, Odense University, Denmark.
Pedersen
E B
EB
Jensen
L V
LV
Nielsen
C M
CM
D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis*; D002460:Cell Line; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D015497:HIV-1 / Q000187:drug effects; D011817:Rabbits; D018139:Simplexvirus / Q000187:drug effects
D000998:Antiviral Agents; D015224:Dideoxynucleosides