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Synthesis of sugar-modified 4'-thiocytidine derivatives
D Kaga1, N Minakawa, A Matsuda
1Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Nucleic Acids Research. Supplement (2001)
|July 3, 2003
Abstract:
An improved and large-scale synthesis of 1,4-anhydro-2,3,5-tri-O-benzyl-4-thio-D-ribitol (4) has been achieved via dibromination of 2,3,5-tri-O-benzyl-D-ribitol (1). Using the Pummerer reaction, 4'-thiocytidine derivative (10) was successfully prepared in multigram scale. After deprotection of the 2,4-dimethoxybenzoyl group of 10, the resulting 11 was converted into 2'-deoxy-4'-thiocytidine (16) via the radical deoxgenation. The sugar-modified 4'-thiocytidine derivatives, 17 and 18, were also prepared.