133782-81-7Relevant articles and documents
Synthesis of pyrimidine 2′-deoxy ribonucleosides branched at the 2′-position via radical atom-transfer cyclization reaction with a vinylsilyl group as a radical-acceptor tether
Sukeda,Shuto,Sugimoto,Ichikawa,Matsuda
, p. 8988 - 8996 (2007/10/03)
Recently, we developed a regio- and stereoselective method for introducing a vinyl group at the position β to a hydroxyl group in halohydrins or α-phenylselenoalkanols via a radical atom-transfer cyclization reaction with a vinylsilyl group as a temporary connecting radical-acceptor tether. The synthesis of 2′-deoxy-2′-C-vinyl- and 2′-deoxy-2′-C-hydroxymethyluridines (7 and 8, respectively) and the corresponding 2′-deoxycytidine congeners (10 and 11, respectively), which were designed as potential antitumor and/or antiviral agents, was achieved using this radical atom-transfer cyclization as the key step. When the 2′-deoxy-2′-iodo-5′-O-monomethoxytrityl (MMTr) uridine derivative 19a, bearing a vinylsilyl group at the 3′-hydroxyl group, was heated with (Me3Sn)2 and AIBN in benzene, the corresponding radical atom-transfer product was generated, which in turn was successively treated with tetrabutylammonium fluoride and TBSCI/imidazole to give the desired 2′-deoxy-5′-O-MMTr-3′-O-TBS-2′-C-vinyluridine (25). Compound 25 was successfully converted into the target 2′-deoxy-2′-branched pyrimidine ribonucleosides 7, 8, 10, and 11.
Intramolecular cyclization-trapping of carbon radicals by olefins as means to functionalize 2′- and 3′-carbons in β-D-nucleosides
Wu,Xi,Gioeli,Chattopadhyaya
, p. 2237 - 2254 (2007/12/18)
Intramolecular free-radical addition-cyclization reactions of 1-(5′-O-(MMTr)-3′-deoxy-3′-phenylseleno-2′-O-allyl- or 2′-O-alkynyl-β-D-arabinofuranosyl)uracils 6a - 6d, 1-(5′O-(MMTr)-2′-deoxy-2′-phenylseleno-3′-O-allyl- or 3′-O-alkynyl-β-D-xylofuranosyl)ur
