Synthesis of sugar-modified 4'-thiocytidine derivatives.
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.
Kaga
D
D
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Minakawa
N
N
Matsuda
A
A
D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D012255:Ribitol / Q000031:analogs & derivatives / Q000737:chemistry; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D013872:Thionucleosides; D003841:Deoxycytidine; C070453:2'-deoxy-4'-thiocytidine; D012255:Ribitol