651718-75-1Relevant articles and documents
N-Glycosylation of 2,3-dideoxyfuranose derivatives having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position
Murano, Tetsuo,Yuasa, Yoko,Muroyama, Soichiro,Yokomatsu, Tsutomu,Shibuya, Shiroshi
, p. 9059 - 9073 (2007/10/03)
Lewis acid-mediated N-glycosylation of 2,3-dideoxyribofunanosides having a (diethoxyphosphorothioyl)difluoromethyl group at the 3α-position with silylated nucleobases was examined. The phosphorothioyldifluoromethyl was found to be an effective functional group for the diastereoselective synthesis of β-N1-pyrimidine-nucleotide analogues 26 and 28-30. However, the method was not useful for the diastereoselective synthesis of adenine nucleotide analogues. The nucleotide analogue 26 was transformed to the difluoromethylenephosphonate analogue 31 of thymidine-3′-phosphate by oxidation with m-CPBA, followed by aqueous work-up.