PubMed · 10559502
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A Marruchella, M Tondini. 1999. Gemcitabine toxicity.. https://doi.org/10.1378/chest.116.5.1491
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We report the synthesis of the fluorescent 2'-deoxycytidine analogue 5-methylpyrimidin-2-one nucleoside, its incorporation at three specified sites in a single 60-nucleotide DNA molecule, and the use of its total and polarized intrinsic fluorescence to characterize RecA-DNA complexes. [reaction: see text]
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.
A facile stereospecific synthetic method for alpha-anomeric 2'-deoxypyrimidine nucleoside unit utilizing aminooxazoline derivative of ribofuranose was investigated. Thus, easily accessible riboaminooxazoline derivative prepared by ribose and cyanamid was allowed to react with ethyl alpha-bromoethylacrylate to give corresponding adduct. The adduct was cyclized by strong base such as potassium t-butokiside. The resulted 2,2'-cyclonucleoside was then treated with acetyl bromide followed by n-butyltin hydride to give alpha-anomeric 3',5'-di-O-acetylthymidine. 3',5'-Di-O-acety groups of the nucleoside were easily removed by the action of excess of triethyl amine in methanol. Essentially same procedure afforded corresponding 2'-deoxyuridine, which was further, converted to alpha-anomeric 2'-deoxycytidine.