28734-85-2Relevant articles and documents
Studies toward the oxidative and reductive activation of C-S bonds in 2′-S-aryl-2′-thiouridine derivatives
Rayala, Ramanjaneyulu,Giuglio-Tonolo, Alain,Broggi, Julie,Terme, Thierry,Vanelle, Patrice,Theard, Patricia,Médebielle, Maurice,Wnuk, Stanislaw F.
, p. 1969 - 1977 (2016/04/05)
Studies directed toward the oxidative and reductive desulfurization of readily available 2′-S-aryl-2′-thiouridine derivatives were investigated with the prospect to functionalize the C2′-position of nucleosides. The oxidative desulfurization-difluorination strategy was successful on 2-(arylthio)alkanoate surrogates, while extension of the combination of oxidants and fluoride sources was not an efficient fluorination protocol when applied to 2′-S-aryl-2′-thiouridine derivatives, resulting mainly in C5-halogenation of the pyrimidine ring and C2′-monofluorination without desulfurization. Cyclic voltammetry of 2′-arylsulfonyl-2′-deoxyuridines and their 2′-fluorinated analogues showed that cleavage of the arylsulfone moiety could occur, although at relatively high cathodic potentials. While reductive-desulfonylation of 2′-arylsulfonyl-2′-deoxyuridines with organic electron donors (OEDs) gave predominantly base-induced furan type products, chemical (OED) and electrochemical reductive-desulfonylation of the α-fluorosulfone derivatives yielded the 2′-deoxy-2′-fluorouridine and 2′,3′-didehydro-2′,3′-dideoxy-2′-fluorouridine derivatives. These results provided good evidence of the generation of a C2′-anion through carbon-sulfur bond cleavage, opening new horizons for the reductive-functionalization approaches in nucleosides.
Benzhydryl as an efficient selective nitrogen protecting group for uracils
Wu, Fan,Buhendwa, Musole G.,Weaver, Donald F.
, p. 9307 - 9309 (2007/10/03)
Regioselective N-substitution of the less active nitrogen within uracil analogues has been achieved following preliminary N-protection at the more active N-position with a benzhydryl protecting group. This protecting group is stable to concentrated HCl (a
Solid-phase synthesis of 4(1H)-quinolone and pyrimidine derivatives based on a new scaffold - Polymer-bound cyclic malonic acid ester
Huang, Xian,Liu, Zhanxiang
, p. 6731 - 6737 (2007/10/03)
An efficient method for the preparation of polymer-bound cyclic malonic acid ester starting from Merrifield resin has been developed. Reaction of the resin-bound cyclic malonic acid ester with triethyl orthoformate and subsequent double substitution with
