101527-67-7Relevant articles and documents
Radical-mediated furanose ring reconstruction from 2′,3′-seco-uridine
Kumamoto, Hiroki,Ogamino, Junko,Tanaka, Hiromichi,Suzuki, Hisaki,Haraguchi, Kazuhiro,Miyasaka, Tadashi,Yokomatsu, Tsutomu,Shibuya, Shiroshi
, p. 3331 - 3341 (2007/10/03)
Starting from 5′-O-trityl-2′,3′-seco-uridine, reconstruction of a furanose structure was carried out by the following sequence of reactions: (1) regioselective introduction of a phenylselenenyl group to the 2′-position of the 2′,3′-seco-uridine, (2) oxidation and subsequent Wittig reaction of the 3′-hydroxyl group and (3) intramolecular radical reaction (5-exo-trig ring closure) leading to 3′-C-carbon-substituted 2′,3′-dideoxyuridine. Also studied is the Pummerer reaction of the 2′-phenylseleno derivative of 2′,3′-seco-uridine. The resulting product, an α-(acyloxy)phenylselenide, also serves as a substrate for the radical cyclization to allow the introduction of a hydroxyl group at the 2′-position of the reconstructed furanose ring.
From nucleosides, their acyclo- and anhydro-analogues to chiral complementary lariat ethers
Skaric,Caplar,Skaric,Zinic
, p. 1821 - 1824 (2007/10/02)
Novel 2',5'-(5), 2',3'-(13), 3',5'-anhydro-2',3'-seco-uridine (9) and syn-18-hydroxymethyl-2-[uracil-1-yl(20) and 2-adenin-9-yl(21)]-18-crown-6-ether, have been efficiently prepared from the respective, properly protected and activated 2',3'-seco-nucleosi
The Chemistry of 2',3'-Seconucleosides. 1. Synthesis and Chemical and Biological Properties of Derivatives of 2',3'- Secouridine
Jones, A. Stanley,Walker, Richard T.,Wyatt, Paul G.,Balzarini, Jan,Clercq, Erik De
, p. 3520 - 3532 (2007/10/02)
Aspects of the chemistry of 2',3'-secouridine (1-(R)-1,5-dihydroxy-4-hydroxymethyl-3-oxapent-2-yl)uracil) derivatives have been studied. 5'-O-Trityl-2',3'-secouridine (4) was obtained from 5'-O-trityluridine by oxidation with periodate followed by reducti
