TY - JOUR
T1 - Nucleosides. 125. Synthesis of 5'-deoxy-5'-substituted-1,3-dimethyl-psi-uridines from 3',5'-O-(1,1,3,3-tetraisopropyldisiloxanyl)-1,3-dimethyl-psi-uridine. A novel isomerization reaction.
AU - Pankiewicz, K. W.
AU - Watanabe, K. A.
PY - 1982
Y1 - 1982
N2 - Treatment of 3'-5'-O-(1,1,3,3-tetraisopropyldisiloxanyl)-1,3-dimethyl-psi-uridine (7) . with one equivalent of base and a slight excess of trifluoromethanesulfonic anhydride afforded 5'-O-trifluoromethanesulfonyl-2',3'-O-(1, 1,3,3-tetraisopropyldisiloxanyl)-1,3-dimethyl-psi-uridine (8). Nucleophilic displacement of the 5'-trifluoromethanesulfonyloxy group by treatment with various alkali metal salts of halide, azide, or acetate followed by deprotection by fluoride ion treatment afforded the corresponding 5'-substituted-1, 3-dimethyl-psi-uridine derivatives (10) in good yields in crystalline form.
AB - Treatment of 3'-5'-O-(1,1,3,3-tetraisopropyldisiloxanyl)-1,3-dimethyl-psi-uridine (7) . with one equivalent of base and a slight excess of trifluoromethanesulfonic anhydride afforded 5'-O-trifluoromethanesulfonyl-2',3'-O-(1, 1,3,3-tetraisopropyldisiloxanyl)-1,3-dimethyl-psi-uridine (8). Nucleophilic displacement of the 5'-trifluoromethanesulfonyloxy group by treatment with various alkali metal salts of halide, azide, or acetate followed by deprotection by fluoride ion treatment afforded the corresponding 5'-substituted-1, 3-dimethyl-psi-uridine derivatives (10) in good yields in crystalline form.
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M3 - Article
C2 - 7183977
AN - SCOPUS:0020439709
SN - 0261-3166
SP - 9
EP - 12
JO - Nucleic acids symposium series
JF - Nucleic acids symposium series
IS - 11
ER -