192999-30-7Relevant academic research and scientific papers
Synthesis of Racemic and Enantiomerically Pure 2′-Thia-2′,3′dideoxycytidine as Potential Anti-Hepatitis B Virus Agents
Pan, Bai-Chuan,Cheng, Yung-Chi,Chu, Shih-Hsi
, p. 909 - 915 (2007/10/03)
A novel class of nucleosides with the C1′ atom bonded to three hetero atoms was synthesized. 2′-Thia2′,3′-dideoxycytidine was the pilot compound of this series. (±)-β-2′-Thia-1′,3′-dideoxycytidine (6) and (±)-α-2′-thia-2′,3′-dideoxycytidine (7) were synthesized from (±)-3-mercapto-1,2-propanediol. The synthesis of the enantiomerically pure 2′-thia-2′3′-dideoxycytidines (α-D-form, β-D-form, α-L-form and β-L-form) from optically pure (S)-(2,2-dimethyl-1,3-dioxalan-yl)methyl p-toluenesulfonate (8) and its (R)-isomer 18 was also described. The preliminary biological results showed that (+)-β-D-2′-thia-2′,3′-dideoxycytidine (26) was the most active against human hepatitis B virus with an ED50of 3μM.
Stereocontrol in the Intramolecular Nitrone Cycloaddition to Vinyl Sulphur Derivatives.
Annunziata, Rita,Cinquini, Mauro,Cozzi, Franco,Giaroni, Paola,Raimondi, Laura
, p. 251 - 264 (2007/10/02)
The intramolecular cycloaddition to vinyl sulphur derivatives of a series of nitrones featuring an alkyl or alkoxy substituted α-stereocenter on the tether connecting dipol and dipolarophile occurs in a competely stereoselective fashion to give 3',3-anti configurated products.The synthetic potentialities of this reaction is illustrated by the synthesis of a precursor of (d)-biotin.
