62410-12-2Relevant academic research and scientific papers
Synthesis of new ribosylated Asn building blocks as useful tools for glycopeptide and glycoprotein synthesis
Bonache, M. Angeles,Nuti, Francesca,Le Chevalier Isaad, Alexandra,Real-Fernández, Feliciana,Chelli, Mario,Rovero, Paolo,Papini, Anna M.
, p. 4151 - 4153 (2009)
We performed the first synthesis of new Asn derivatives bearing α- or β-ribose as pure anomers, linked by an N-glycosidic bond, on the side chain of the Asn residue orthogonally protected for Fmoc/tBu SPPS, by an efficient five-step strategy with a global yield of 73% starting from d-ribose. These building blocks are obtained in a large scale and can be useful tools for glycopeptide and glycoproteins synthesis.
Short-step anodic access to emissive RNA homonucleosides
Okada, Yohei,Shimada, Kouhei,Kitano, Yoshikazu,Chiba, Kazuhiro
, p. 1371 - 1375 (2014)
Emissive RNA homonucleosides were added to the growing library of synthetic probes. The emissive nucleobases were constructed in one step from the methallyl C-glycoside of D-ribofuranose, which was prepared stereoselectively. The homonucleosides displayed various emission colors by using a single excitation wavelength that could be fine-tuned merely by changing the carbonyl substituent on the methoxyphenol. Emissive RNA homonucleosides are added to the growing library of synthetic probes. The emissive nucleobases are constructed in one step from the methallyl C-glycoside of D-ribofuranose, which is prepared stereoselectively. The homonucleosides display various emission colors by using a single excitation wavelength. Copyright
NUCLEOSIDE SYNTHESIS: A SYSTEMATIC STUDY OF THE INFLUENCE OF THE NATURE AND STEREOCHEMISTRY OF D-ALDOPENTOFURANOSES, AND THE EFFECT OF THE SUBSTITUENT AT C-2, IN THE ACID-CATALYZED FUSION-REACTION WITH INDAZOLE
Kam, Bernard L.,Barascut, Jean-Louis,Imbach, Jean-Louis
, p. 285 - 294 (1980)
A systematic study of the acid-catalyzed fusion-reaction is reported.The influence of the nature and stereochemistry of the D-aldopentofuranose and the effect of the substituent at C-2 have been investigated by using indazole as a model heterocycle.The results obtained show that the nature and stereochemistry of the staring, per-O-acetylated D-aldopentofuranose have no significant effect upon the product distribution of the acid-catalyzed fusion-reaction.The use of a sugar lacking a participating group at C-2 showed, however, that the absence of participation increases the ratio of cis-1',2'-nucleosides, and the mechanism involved is discussed.In all cases, the results indicated that the distribution of the products is determined by their relative, thermodynamic stabilities.
Synthesis, antiviral and antitumor activities investigations of a series of Ribavirin C-nucleoside analogue prodrugs
Ferraris, Olivier,Gallier, Florian,Lecouvey, Marc,Migianu-Griffoni, Evelyne,Ouarti, Abdelhakim,Peyrefitte, Christophe,Sabat, Nazarii,Uziel, Jacques,Lubin-Germain, Nadège
, (2022/03/15)
Phosphoramidates obtained according to the ProTide strategy are known for their ability to increase the biological activity of various nucleosides. A series of such prodrugs of SRO-91, a non-natural ribofuranosyl-1,2,3-triazole C-nucleoside obtained by a synthetic sequence involving an indium mediated alkynylation and a Huisgen cycloaddition, was prepared and the antitumor activity on 3 strains of tumor cells was investigated. Two compounds 9a and 9c exhibited interesting cell proliferative inhibitions (IC50 = 2.5–12.1 μM) on two cell lines (pancreas and lung). Moreover, concerning the antiviral activity, another phosphoramidate 14 bearing a different aryl masking group exhibited an IC50 of 5 μM on Crimean-Congo Hemorrhagic Fever orthonairovirus. In both cases, free SRO-91 presented no activity on these cell lines.
Short-Step Anodic Access to Emissive RNA Homonucleosides
Okada, Yohei,Shimada, Kouhei,Kitano, Yoshikazu,Chiba, Kazuhiro
, p. 1371 - 1375 (2015/10/05)
Emissive RNA homonucleosides were added to the growing library of synthetic probes. The emissive nucleobases were constructed in one step from the methallyl C-glycoside of D-ribofuranose, which was prepared stereoselectively. The homonucleosides displayed various emission colors by using a single excitation wavelength that could be fine-tuned merely by changing the carbonyl substituent on the methoxyphenol.
Peracetylated β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose in the chemical literature: Until now, mirages in the literature
Martinez, Heike Otero,Reinke, Helmut,Michalik, Dirk,Vogel, Christian
body text, p. 1834 - 1840 (2010/02/28)
The peracetylated β-allyl C-glycosides of D-ribofuranose (8) and 2-deoxy-D-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined. Georg Thieme Verlag Stuttgart.
D-RIBOFURANOSYL AZIDES. A DIRECT CONVERSION OF 1-O-ACYL-2,3-O-ISOPROPYLIDENE-D-RIBOFURANOSE INTO D-RIBOFURANOSYL AZIDES
Logue, Marshall W.,Han, Byung Hee
, p. 287 - 298 (2007/10/02)
Reactions of azidotrimethylsilane with 1-O-acetyl-2,3,5-tri-o-benzoyl-β-D-ribofuranose (2), and the 1,5-di-O-p-nitrobenzoyl and 1,5-di-O-acetyl derivatives, 4 and 5 respectively, of 2,3-O-isopropylidene-β-D-ribofuranose, in the presence of the Lewis acids
