115459-50-2Relevant articles and documents
A Stereocontrolled Synthesis of 1,3,6-Tri-O-benzoyl-α-D-ribofuranose
Brodfuehrer, Paul R.,Sapino, Chester,Howell, Henry G.
, p. 2597 - 2598 (1985)
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).
Effects of 5-O-Ribosylation of Aminoglycosides on Antimicrobial Activity and Selective Perturbation of Bacterial Translation
Herzog, Ido M.,Louzoun Zada, Sivan,Fridman, Micha
supporting information, p. 8008 - 8018 (2016/11/15)
We studied six pairs of aminoglycosides and their corresponding ribosylated derivatives synthesized by attaching a β-O-linked ribofuranose to the 5-OH of the deoxystreptamine ring of the parent pseudo-oligosaccharide antibiotic. Ribosylation of the 4,6-disubstituted 2-deoxystreptamine aminoglycoside kanamycin B led to improved selectivity for inhibition of prokaryotic relative to cytosolic eukaryotic in vitro translation. For the pseudodisaccharide aminoglycoside scaffolds neamine and nebramine, ribosylated derivatives were both more potent antimicrobials and more selective to inhibition of prokaryotic translation. On the basis of the results of this study, we suggest that modification of the 5-OH position of the streptamine ring of other natural or semisynthetic pseudodisaccharide aminoglycoside scaffolds containing an equatorial amine at the 2′ sugar position with a β-O-linked ribofuranose is a promising avenue for the development of novel aminoglycoside antibiotics with improved efficacy and reduced toxicity.
Synthesis of novel 6-substituted thymine ribonucleosides and their 3′-fluorinated analogues
Bozhok, Tatyana S.,Sivets, Grigorii G.,Baranovsky, Alexander V.,Kalinichenko, Elena N.
, p. 6518 - 6527 (2016/09/23)
Nine novel 6-fluorothymine nucleoside analogues of both N(1)-α/β and N(3)-β-ribo series were prepared by the Vorbrüggen method starting from persilylated 6-fluorothymine and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose, 1-O-acetyl-2,5-di-O-benzoyl-3-deoxy-3-fluoro-α,β-D-ribofuranose or 1,2,3,5-tetra-O-benzoyl-β-D-ribofuranose and its α-anomer. Protected N(3)-β-D-ribofuranosides were prepared as sole products in high yields at room temperature. A mixture of benzoylated N(1)-β- and α-anomeric ribonucleosides was obtained at lower temperatures. Yields of β-anomers and stereoselectivities (β:α=2.2/4.5:1) of the condensation reactions depended on reaction conditions and the structure of the glycosylating agent. Debenzoylation of 6-fluorothymine N(1)- or N(3)-β-D-ribofuranosides and their 3′-fluorodeoxy analogues by LiOH monohydrate in MeCN/H2O resulted in the corresponding fluorinated nucleosides in good yields, whereas the deprotection of N(1)-α-ribofuranosides under the same conditions unexpectedly yielded 6,2′-O-α-D-anhydronucleosides. 6-Substituted (OMe, NH2) thymine β-ribonucleosides were prepared by the treatment of protected N(1)-β-D-ribosides with nucleophilic agents.
SYNTHETIC INTERMEDIATE OF 1-(2-DEOXY-2-FLUORO-4-THIO-?-D-ARABINOFURANOSYL)CYTOSINE, SYNTHETIC INTERMEDIATE OF THIONUCLEOSIDE, AND METHOD FOR PRODUCING THE SAME
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Paragraph 1600-1601, (2015/06/10)
A compound represented by a formula [1D] as shown below (wherein R1A, R1B, R2A, R2B, R3A and R3B represent a hydrogen atom, an optionally substituted C1-6 alkyl group, and the li
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 RIBOFURANOSIDES BY CATALYSIS WITH LEWIS ACIDS. GLYCOSIDATION VERSUS TRANSACETYLATION
Chiu-Machado, Ivan,Castro-Palomino, Julio C.,Madrazo-Alonso, Odalys,Lopetegui-Palacios, Carlos,Verez-Bencomo, Vicente
, p. 551 - 562 (2007/10/02)
Several ribofuranosyl derivatives bearing trichloroacetimidoyl or acetyl leaving groups in a Lewis acid promoted ribosylation reaction were prepared and used in an attempt to improve the yield and to avoid donor -> acceptor transacetylation.Trichloroaceti
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.
