Preparation of thianucleoside derivatives.
1'-Deoxy-4'-thioribonucleoside 1 was synthesized from acyclic allylic alcohol 2 by 8 steps. TMSOTf and SnCl4 were found to be a good mediator for the key coupling of thiafuranose part with pyrimidine base to give beta-isomer preferentially.
Uenishi
J
J
Department of Chemistry, Okayama University of Science, Japan.
Motoyama
M
M
Takahashi
K
K
D000433:1-Propanol / Q000737:chemistry; D003857:Deoxyuridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D020005:Propanols; D011743:Pyrimidines / Q000737:chemistry; D013891:Thiouridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D014001:Tin / Q000737:chemistry; D017971:Tin Compounds
D020005:Propanols; D011743:Pyrimidines; D017971:Tin Compounds; C070455:2'-deoxy-4'-thiouridine; D013891:Thiouridine; C023599:stannous chloride; C006463:allyl alcohol; D014001:Tin; D000433:1-Propanol; D003857:Deoxyuridine