Electrooxidative glycosylation through C-S bond cleavage of 1-arylthio-2,3-dideoxyglycosides. Synthesis of 2',3'-dideoxynucleosides.
[reaction: see text] The electrooxidative glycosylation of newly designed 1-arylthio-substituted 2,3-dideoxyglycosides is described. The halide salt-mediated electrooxidation utilizing either of the alpha- or beta-thiodideoxyglycosides proceeded smoothly at -78 degrees C to give dideoxynucleosides in a beta-selective manner, presumably through a 1-halo-substituted glycosyl donor.
Mitsudo
Koichi
K
Department of Applied Chemistry, Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-Naka, Okayama 700-8530, Japan.
Kawaguchi
Takashi
T
Miyahara
Seiji
S
Matsuda
Wataru
W
Kuroboshi
Manabu
M
Tanaka
Hideo
H
D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D015224:Dideoxynucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D006031:Glycosylation; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013865:Thioglycosides / Q000737:chemistry*
D019380:Anti-HIV Agents; D015224:Dideoxynucleosides; D013865:Thioglycosides