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.
Regioselective Transformations of 2',3'-Seconucleosides into Anhydro Structures and Chiral Crown Ethers
Skaric, Vinko,Caplar, Vesna,Skaric, Durdica,Zinic, Mladen
, p. 493 - 506 (2007/10/02)
Intramolecular cyclisation of properly protected and activated derivatives of 2',3'-secouridine (= 1--ethyl>uracil; 1) provided access to the 2,2'-, 2,3'-, 2,5'-, 2',5'-, 3',5'-, and 2',3-anhydro-2',3'-secouridines 5, 16, 17, 26, 28 and 31, respectively (Schemes 1-3).Reaction of 2',5'-anhydro-3'-O-(methylsulfonyl)- (25) and 2',3'-anhydro-5'-O-(methylsulfonyl)-2',3'-secouridine (32) with CH2Cl2 in the presence of 1,8-diazabicycloundec-7-ene generated the N(3)-methylene-bridged bis-uridine structure 37 and 36, respectively (Scheme 3).Novel chiral 18-crown-6 ethers 40 and 44, containing a hydroxymethyl and a uracil-1-yl or adenin-9-yl as the pendant groups in a 1,3-cis relationship, were synthesized from 5'-O-(triphenylmethyl)-2',3'-secouridine (2) and 5'-O,N6-bis(triphenylmethyl)-2',3'-secoadenosine (41) on reaction with 3,6,9-trioxaundecane-1,11-diyl bis(4-toluenesulfonate) and detritylation of the thus obtained (triphenylmethoxy)methyl compound 39 and 43, respectively (Scheme 4).
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
NUCLEOSIDE ANALOGUES WITH A 1,4-DIOXANE, 1,4-OXATHIANE OR 1,4-OXAZINE RING STRUCTURE AS THE CARBOHYDRATE FRAGMENT
Aerschot, Arthur Van,Janssen, Gerard,Herdewijn, Piet
, p. 769 - 777 (2007/10/02)
Pyrimidine and purine nucleoside analogues with a 1,4-dioxane, 1,4-oxathiane or 1,4-oxazine ring structure have been prepared from the corresponding dimesylated seconucleosides by treatment with either sodium hydroxide, sodium sulfide or primary alkylamines.
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
