54946-48-4Relevant articles and documents
Synthesis of a 3′-Fluoro-3′-deoxytetrose Adenine Phosphonate
De, Swarup,De Jonghe, Steven,Herdewijn, Piet
, p. 9464 - 9478 (2017/09/23)
A new synthetic route to a 3′-fluoro-3′-deoxytetrose adenine phosphonate has been developed. The synthesis starts from l-xylose and key steps include the stereospecific introduction of the phosphonomethoxy group and adenine. In addition, a regioselective
An unexpected rearrangement of pent-4-enofuranosides to cyclopentanones upon hydrogenolysis of the anomeric benzyl group
Nie, Shenyou,Chen, Xiaoping,Ma, Yuyong,Li, Wei,Yu, Biao
supporting information, p. 36 - 40 (2016/07/07)
During our synthesis toward the unique nucleoside antibiotic A201A, we were surprised to find that a benzyl arabino-pent-4-enofuranoside underwent a Ferrier II-like rearrangement readily to provide the corresponding cyclopentanone derivative in high yield and stereoselectivity upon hydrogenolysis of the anomeric benzyl group.
Synthesis of alkylcarbonate analogs of O-acetyl-ADP-ribose
Dvorakova, Marcela,Nencka, Radim,Dejmek, Milan,Zbornikova, Eva,Brezinova, Anna,Pribylova, Marie,Pohl, Radek,Migaud, Marie E.,Vanek, Tomas
, p. 5702 - 5713 (2013/09/12)
The non-hydrolyzable alkylcarbonate analogs of O-acetyl-ADP-ribose have been synthesized from the phosphorylated ribose derivatives after coupling with AMP morpholidate promoted by mechanical grinding. The analogs were assessed for their ability to inhibi
Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates
Schmalisch, Sebastian,Mahrwald, Rainer
supporting information, p. 5854 - 5857 (2013/12/04)
Organocatalyzed direct glycosylation of unprotected and unactivated carbohydrates is reported. This process is catalyzed by triphenylphosphine and tetrabromomethane at room temperature under neutral conditions. With this operationally simple protocol thermodynamically favored, glycosides were obtained in a very straightforward reaction.
Kinetic solvent deuterium isotope effect in transesterification of RNA models
Virtanen, Noora,Polari, Lauri,Vaelilae, Maria,Mikkola, Satu
, p. 385 - 397 (2007/10/03)
2-Methylbenzimidazole ribonucleoside arylphosphates (1a,b) and alkylphosphates (2a,b) were synthesized as RNA model compounds containing a minimised number of exchangeable protons. Intramolecular transesterification of these substrates was studied in H2O and D2O solutions over a wide pL range and apparent kinetic solvent deuterium isotope effects of the alkaline cleavage of both substrates and of the cleavage and isomerisation of 2a under neutral and acidic conditions were determined. The observed K H2O/kD2O of 4.9 obtained for the alkaline cleavage of the arylphosphate 1b can be primarily attributed to the ΔpK of the attacking nucleophile. The alkyl leaving group in 2a brings about an additional 1.5-fold isotope effect (kH2O/kD2O of 7.1 observed), which, considering the pL-dependence of the reaction, can not be explained by a process involving a proton transfer. Differences in solvation of the transition state are tentatively suggested as a source of the difference. In contrast to alkaline cleavage, under neutral and acidic conditions the cleavage and isomerisation of 2a showed no apparent solvent isotope effect. Several examples found in the literature show that intramolecular proton transfer from phosphate to the leaving group in pre-equilibria may not necessarily result in an observable solvent isotope effect. This may also explain the results obtained in the present work, since intramolecular proton transfer processes take place in transesterification reactions of 2a under neutral and acidic conditions. Relevance of the results obtained in the base catalysed cleavage to hammerhead ribozyme reaction is briefly discussed. Copyright
Method for producing beta-D-ribofuranose derivatives or optical isomers thereof
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, (2008/06/13)
The present invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzy
Method for producing a beta-D-ribofuranose derivative or an optical isomer thereof
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Example 2, (2010/01/31)
The invention provides a method for efficiently producing β-D-ribofuranose derivatives or optical isomers thereof, useful as synthetic intermediates of pharmaceutical nucleic acid-series products. The method comprises a step of producing 1-O-benzyl-β-D-ri
Readily available carbohydrate-derived imines and amides as chiral ligands for asymmetric catalysis
Pigro, Maria Cristina,Angiuoni, Gabriella,Piancatelli, Giovanni
, p. 5459 - 5466 (2007/10/03)
An easy and diastereoseletive strategy for the synthesis of a new tetrahydrofuranic chiral aldehyde and a new tetrahydrofuranic acid derived from D-ribose is reported. These compounds have been shown to be useful starting materials for obtaining a never d
Synthesis and properties of flavin ribofuranosides and flavin ribopyranosides
Schwoegler, Anja,Gramlich, Volker,Carell, Thomas
, p. 2452 - 2463 (2007/10/03)
Ribose-containing coenzymes like flavin mononucleotide (FMN) can be considered to be fossils of a prebiotic RNA world in which RNA encoded genetic information and catalyzed chemical reactions. To investigate the catalytic and base-pairing properties of FM
Efficient synthesis of 2′-O-alkyl ribonucleosides using trichloroacetimidateDribofuranosides as ribosyl donors
Chanteloup, Luc,Thuong, Nguyen T.
, p. 877 - 880 (2007/10/02)
Trichloroacetimidate-2-O-alkyl-3,5-O-TIPS-β- D-ribofuranoside glycosylates silylated nucleobases in a fast high-yielding and stereo selective reaction promoted by trimethylsilyl trifluoromethanesulfonate. This method has been applied to the syn