22224-41-5Relevant articles and documents
Total synthesis of 2'-O-methyl-β-L-arabinosyluridine and reassignment the nucleoside from penicillium sp. as 2'-O-methyl-β-L-uridine
Shen, Chunyang,Ding, Haixin,Tao, Xueping,Yang, Ruchun,Bai, Jiang,Cao, Ban-Peng,Peng, Yi-Yuan,Xiao, Qiang
, p. 68 - 72 (2020/01/30)
In order to validate the structure of a rarely reported naturally occurring nucleoside isolated from the broth of Penicillium sp. (NO. 64), practical syntheses of 2′-O-methyl-β-L-arabinosyluridine, 2′-O-methyl-α-L-arabinosyluridine, and 2′-O-methyl-β-L-uridine were accomplished. Comparing their nuclear magnetic resonance (NMR) spectra and physical data, its structure was reassigned as 2′-O-methyl-β-L-uridine instead of former reported 2′-O-methyl-β-L-arabinosyluridine.
Branching of poly(ADP-ribose): Synthesis of the Core Motif
Kistemaker, Hans A. V.,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.
, p. 4328 - 4331 (2015/09/15)
The synthesis of the core motif of branched poly(adenosine diphosphate ribose) (poly(ADPr)) is described, and structural analysis reasserted the proposed stereochemistry for branching. For the synthesis, a ribose trisaccharide was first constructed with only α-O-glycosidic linkages. Finally, the adenine nucleobase was introduced via a Vorbrüggen-type glycosylation reaction. The orthogonality of the selected protecting groups was demonstrated, allowing for the construction of branched poly(ADPr) oligomers in the near future.
2'-FLUORO-4'-SUBSTITUTED NUCLEOSIDES, THE PREPARATION AND USE
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Page/Page column 11, (2010/05/13)
The present invention provides 2'-fluorine-4'-substituted-nucleoside analogues or their pro-drugs or 5'-phosphate esters (including the pro-drugs of the 5'-phosphate esters), preparation methods and uses thereof. The compounds have the general formula as follows: wherein: R = CH3, CH, N3, C≡CH; R' = H, F; X = F, OH, NH2; Y = H, CH3, F, OH, NH2 The compounds are used in the synthesis of drugs for the treatment of virus infection, especially for the treatment of HBV, HCV or HIV infection.
Synthesis of 2-deoxy-2-fluoro-arabinose derivatives
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, (2008/06/13)
A process for deoxofluorinating a C2-hydroxyl group of a furanose, includes: (a) mixing the furanose and a deoxofluorinating agent in a solvent to form a reaction mixture, and (b) heating the reaction mixture to greater than about 50° C. The process provides deoxofluorinated products, such as 2-fluoro-arabinoses, in yields of at least 80% of theoretical.
Studies on the origin of stereoselectivity in the synthesis of 1,2-trans glycofuranosyl azides
Stimac, Anton,Kobe, Joze
, p. 149 - 160 (2007/10/03)
The stereoselectivity of the 1,2-trans directed, Lewis acid-catalysed azidation of peracylated furanoses was found to depend on the reactivity of the azide donor (azide nucleophilicity) and the configuration at the anomeric centre relative to the neighbouring 2-O-acyl group. Reactions of 1,2-trans glycosyl esters with highly nucleophilic azide donors, generated from SnCl4 and Me3SiN3, were stereospecific. The results are interpreted in terms of the rapid reaction of the azide species with bicyclic 1,2-acyloxonium (1,2-O-alkyliumdiyl-D-glycofuranose) ions, which were the primarily formed reactive intermediates. When using 1,2-cis glycosyl esters as starting materials the selectivity was reduced (90-94% de); the same is true with 1,2-trans counterparts if less nucleophilic Me3SiN3 in combination with Me3SiOTf catalyst was used. This occurred due to the appearance of the more reactive but less selective oxocarbenium (glycofuranoxonium) ions either as primarily formed reactive intermediates in the former case or after equilibration with acyloxonium ions in the latter case. Protected 1,2-trans β-D-glycofuranosyl azides with ribo, xylo and 3-deoxy-erythro-pento configurations were best prepared from the corresponding glycosyl esters using 0.05 equivalents of SnCl4, i.e., under anomerization-free conditions. Azidation of methyl glycofuranosides proceeds with inferior (80-90% de) and less predictable selectivity irrespective of the starting anomeric configuration. Copyright (C) 2000 Elsevier Science Ltd.
6-Methyl-5-azacytidine - Synthesis, conformational properties and biological activity. A comparison of molecular conformation with 5- azacytidine
Hanna, Naeem B.,Zajicek, Jaroslav,Piskala, Alois
, p. 129 - 144 (2007/10/03)
The title compound was prepared by the isocyanate procedure and the trimethylsilyl method. The measurement of 1H NMR spectrum of 6-methyl-5- azacytidine (1) revealed a preference of γ(t) (46%) rotamer around C(5')- C(4') bond, a predominance of N conformation of the ribose ring (K(eq) 0.33) and a preference of syn conformation around the C-N glycosyl bond. An analogous measurement of 5-azacytidine has shown a preference of γ+ (60%) rotamer around the C(5')-C(4') bond, a predominance of N conformation of the fibose ring (K(eq) 0.41) and a preference of anti conformation around the C- N glycosyl bond 6-Methyl-5-azacytidine (1) inhibits the growth of bacteria E coli to the extent of 85% at 4000 μM concentration and the growth of LoVo/L, a human colon carcinoma cell line, to the extent of 30% at 100 μM concentration but did not inhibit L1210 cells at ≤ 100 μM concentration 6- Methyl-5-azacytidine (1) exhibited no in vitro antiviral activity at ≤ 1 μM concentration.
Antiviral Nucleosides. A Stereospecific, Total Synthesis of 2'-Fluoro-2'-deoxy-β-D-arabinofuranosyl Nucleosides
Howell, Henry G.,Brodfuehrer, Paul R.,Brundidge, Steven P.,Benigni, Daniel A.,Sapino, Chester
, p. 85 - 88 (2007/10/02)
A general, total synthesis of (2'-fluoro-2'-deoxy-β-D-arabinofuranosyl)uracils 1a-d is described.A study of the coupling reaction beetwen 3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl bromide (7) and silylated pyrimidines 11a-d has resulted in a high overall yield for the five-step stereospecific synthesis of β-nucleosides.
A Stereocontrolled Synthesis of 1,3,6-Tri-O-benzoyl-α-D-ribofuranose
Brodfuehrer, Paul R.,Sapino, Chester,Howell, Henry G.
, p. 2597 - 2598 (2007/10/02)
The synthesis of a valuable carbohydrate intermediate, 1,3,5-tri-O-benzoyl-α-D-ribofuranose (4), has been achieved in a convenient, one-step process from commercially available 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose (7).
