Synthesis and antiviral evaluation of alpha-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides.
A series of hydroxymethyl branched analogues of antiviral apio d4Ns was synthesized from D-arabinose. The SN2' ring opening reaction of 2,2'-anhydro-alpha-D-pyrimidinenucleoside (10) was mainly investigated. The reaction selectively gave SN2' adducts, which were deprotected to furnish the desired alpha-D-2',3'-didehydro-2',3'-dideoxy-3'-C-hydroxymethyl nucleosides (2).
Yamada
K
K
Biochemicals Division, Yamasa Corporation, 2-10-1 Araoichio, Choshi, Chiba 288-0056, Japan.
Hayakawa
H
H
Sakata
S
S
Yoshimura
Y
Y
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D006900:Hydroxylation; D008745:Methylation; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides