110238-01-2Relevant academic research and scientific papers
Regioselective Transformations of 2',3'-Seconucleosides into Anhydro Structures and Chiral Crown Ethers
Skaric, Vinko,Caplar, Vesna,Skaric, Durdica,Zinic, Mladen
, p. 493 - 506 (1992)
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).
First Hydroxamic Seconucleoside Derivatives
Vrcek, Valerije,Caplar, Vesna,Ursic, Stanko
, p. 119 - 124 (2007/10/03)
Nucleoside analogues possessing hydroxamate moiety were prepared from secouridine derivatives oxidized at C(2')-position. 3',5'-O-Isopropylidene-2',3'-secouridine was oxidized with CrO3/py complex to the carboxylate level and with DMSO/DCC to the aldehyde level. Both compounds (precursors) gave C(2')-nucleoside hydroxamic acids in the reaction with hydroxylamine or nitrosobenzene in the presence of Fe3+ ions, respectively.
