10457-14-4Relevant academic research and scientific papers
Total synthesis of uradl polyoxin c
Kato, Keisuke,Chen, Cheng Yu,Akita, Hiroyuki
, p. 1527 - 1533 (1998)
An improved synthesis of methyl (methyl 5-azido-5deoxy-2,3-O-isopropylidene-β-D-allofuranosid)uronate (7) from methyl 2,3-0-isopropylidene-β-D-rifro-pentodialdo-l,4-furanoside (6), using vinylmagnesium bromide in the key step, and its application to the total synthesis of uracil polyoxin C (1) are described.
A new concept for the preparation of beta-L- and beta-D-2',3'-dideoxynucleoside analogues.
Albert, Martin,De Souza, Dominic,Feiertag, Petra,Hoenig, Helmut
, p. 3251 - 3254 (2002)
[reaction: see text] A new method for the synthesis of 2',3'-dideoxynucleoside analogues has been developed. An electrochemical activation of 2-substituted furans is followed by the coupling with a pyrimidine or purine base. This gives planar furyl nucleosides as key intermediates, which are hydrogenated cis-selectively to give the corresponding beta-2',3'-dideoxynucleosides as racemic mixtures. An enzymatic kinetic resolution gives rise to beta-D- and beta-L-configured derivatives in high optical purity. This is exemplified by the synthesis of beta-D- and beta-L-3'-deoxythymidine.
Bicyclic nucleoside analogues from D-glucose: Synthesis of chiral as well as racemic 1,4-dioxepane ring-fused derivatives
Tripathi, Subhankar,Maity, Joy Krishna,Achari, Basudeb,Mandal, Sukhendu B.
, p. 1081 - 1087 (2005)
The dioxepanofuranose derivatives 4 and 12, obtained through the cyclization of the 3-(2-hydroxyethyl) ether of a d-xylo-pentodialdose derivative, were appropriately functionalized and elaborated to the first examples of the new class of 3′-O and 5′-O-bicyclic nucleoside analogues 9, 10, and 14 with a fused seven-membered ring. Reactions carried out through the intermediacy of the d-xylo-pentodialdose derivative 5 yielded racemic products, while prior protection of the 4-formyl group (as in 7) before deprotection of the 1,2-hydroxyl groups led to optically active analogues.
Concise synthesis and antibacterial evaluation of novel 3-(1,4-disubstituted-1,2,3-triazolyl)uridine nucleosides
Tachallait, Hamza,Bouyahya, Abdelhakim,Talha, Aicha,Bakri, Youssef,Dakka, Nadia,Demange, Luc,Benhida, Rachid,Bougrin, Khalid
, (2018)
We report herein a simple and efficient synthesis of a new series of antibacterial uridine nucleosides. The strategy involved a sequential silylation/N-glycosylation/N-propargylation procedure of uracil 1 for preparing the dipolarophile 5 in good yield. A series of novel uridine-[1,2,3]triazole nucleosides 6a–j were efficiently synthesized via the copper-catalyzed azide–alkyne cycloaddition (CuAAC) from dipolarophile 5 with different selected azides. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvements were observed when reactions were carried out under sonication. Their antibacterial potential has been evaluated by means of a micro-dilution assay against either Gram-positive or Gram-negative bacteria. Compounds 6i and 6j have shown significant bactericidal activity against Staphylococcus aureus (MIC = 10 and 6 μM, respectively), and 6h against Escherichia coli (MIC = 8 μM). Moreover, antibacterial kinetic assays showed that 6i and 6j significantly reduced the S. aureus growth rate at the MIC concentration, after 6 h, compared to their deprotected analogs, 6k and 6l, respectively. Compound 6h also significantly reduced the growth of E. coli. These antibacterial effects may be related to the penetrating properties of these compounds, as revealed by the leakage of nucleic acids from the sensitive strains.
Stereoselective synthesis of novel C-azanucleoside analogues by microwave-assisted nucleophilic addition of sugar-derived cyclic nitrones
Li, Xiaoliu,Qin, Zhanbin,Wang, Rui,Chen, Hua,Zhang, Pingzhu
, p. 1792 - 1798 (2011)
A series of C-azanucleoside analogues were synthesized by microwave-assisted nucleophilic addition of electron-rich hetero-aromatics to sugar-derived cyclic nitrones, and followed by reduction and deprotection. The nucleophilic addition afforded the 2′,3′-trans isomer as the dominant by the favorite exo attack and showed high stereoselectivity in polar solvent.
Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza- nucleosides
Hyrosova,Fisera,Jame,Pronayova,Medvecky,Koos
, p. 10 - 17 (2007)
Two strategies for the synthesis of isoxazolidinyl nucleosides as potential antiviral agents are reported: a one-step approach based on 1,3-dipolar cycloaddition of D-lyxosyl nitrone with N,N-dibenzyl-9-vinyl adenine, and a two-step methodology based on the Vorbrueggen nucleosidation of the 5-acetoxyisoxazolidine. The chiral D-lyxosyl nitrone undergoes regioselective 1,3-dipolar cycloadditions with N,N-dibenzyl-9-vinyl adenine and vinyl acetate giving 5-substituted isoxazolidines as a mixture of four diastereoisomers in good yields. The condensation of 5-acetoxyisoxazolidine with silylated uracil, thymine, and N-acetylcytosine proceeded with moderate to good stereoselectivity with the formation of the expected isoxazolidinyl β-and α-nucleosides.
Synthesis of 3',4'-C-bishydroxymethyl-2',3',4'-trideoxy-β-L-threo- pentopyranosyl nucleosides as potential inhibitors of HIV
Lundquist,Kvarnstrom,Svensson,Classon,Samuelsson
, p. 1493 - 1502 (1995)
The synthesis of 3',4'-bishydroxymethyl-2',3',4'-trideoxy pentopyranosyl derivatives of thymine, uracil, cytosine, and adenine is described. trans- (3S,4S)-Bis(methoxycarbonyl)cyclopentanone (3) was converted to 1-O-acetyl- 3,4-C-bis[(tert-butyldiphenylsiloxy)methyl]-2,3,4-trideoxy-α,β-L-threo- pentopyranose (6), which was subsequently condensed with the silylated purine and pyrimidine bases.
Experimental evidence for intramolecular attractive nonbonded C-F ··· H-C interactions in 2',3'-dideoxy-4'-(fluoromethyl)nucleosides - Through- space J(CF) and J(HF) NMR coupling constants, correlation with empirical parameters of solvent polarity and single-crystal X-ray structures
Mele, Andrea,Vergani, Barbara,Viani, Fiorenza,Meille, Stefano Valdo,Farina, Alessandra,Bravo, Pierfrancesco
, p. 187 - 196 (1999)
A collection of 5'-O-benzyl-2',3'-dideoxy-4'-(fluoromethyl)nucleosides carrying both purinic and pyrimidinic nucleobases (uracil, 5-Br-uracil, 5- O2N-uracil, 6-Cl-purine and inosine) were synthesized in both the α and the β form. Through-space-transmitted 6J(CF) NMR coupling constants between F and C-6 (pyrimidinic base) or C-8 (purinic base) were observed for all of the α anomers of the compounds examined, whilst the corresponding 7J(HF) coupling constants were resolved only for the 5-substituted uracil derivatives. The absolute values of all the through-space couplings were found to decrease monotonically with increasing solvent polarity (CDCl3, MeOD, [D6]acetone, [D6]DMSO). This trend suggests that the through-space interaction is mediated by an intramolecular (sp3)C-F ··· H-C(sp2) hydrogen bond. The possibility of any relevant solvent-induced conformational change influencing the F/base mutual spatial relationship in the molecules investigated was ruled out by heteronuclear steady-state 1H{19F}-NOE experiments. A linear correlation was observed between 6J(CF) and 7J(HF) coupling constants and the Kamlet-Taft's hydrogen bond basicity parameter β. The crystal structures of the α and β anomers of the 5-nitrouracil nucleoside show evidence that the H-6 of the nucleobase forms hydrogen-bond- like interactions involving the O-benzyl oxygen atom in the β anomer, and that in the case of the α anomer this is replaced by the F atom of the fluoromethyl group.
β-Anomer selectivity in 2′-deoxynucleoside synthesis: A novel approach using an acyl carbamate directing group
Young, Robert J.,Shaw-Ponter, Sue,Hardy, George W.,Mills, Gail
, p. 8687 - 8690 (1994)
Glycosylation of silylated pyrimidines using a phenyl 2-deoxy-3-O-(N-benzoyl)carbamoyl-1-thio-D-erythro-pentofuranoside yielded 2-deoxy-β-ribonucleosides in good yields with excellent anomeric selectivity. This prototype 3-O-carbamate directing group was readily formed and removed in high yields.
Effective synthesis of nucleosides utilizing O-acetyl-glycosyl chlorides as glycosyl donors in the absence of catalyst: Mechanism revision and application to silyl-hilbert-johnson reaction
Liang, Chengyuan,Ju, Weihui,Ding, Shunjun,Sun, Han,Mao, Gennian
, (2017)
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield.
