<scp>L</scp>‐Nucleosides

Perrone, Daniela; Capobianco, Massimo L.

doi:10.1002/9781118498088.ch11

Cited by 5 publications

(3 citation statements)

References 185 publications

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“…2-Deoxy- l -ribose also serves as the sugar backbone for preparing unnatural l -DNA, which could be used in studies of nucleic acid recognition with natural d -DNA . Moreover, modified l -deoxyribonucleosides, such as l -FMAU (Clevudine), l -dT (Telbivudine), and val- l -dC (Valtorcitabine), are promising antitumor or antiviral drugs . These modified l -deoxyribonucleosides all contain 2-deoxy- l -ribose as their sugar components.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of l-Deoxyribonucleosides from d-Ribose

2018

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The preparation of 2-deoxy-l-ribose derivatives or mirror image deoxyribonucleosides (l-deoxyribonucleosides) from d-ribose is reported. Starting from inexpensive d-ribose, an acyclic d-form carbohydrate precursor was synthesized to study a unique carbonyl translocation process. In this novel radical reaction, not only was the configuration of the sugar transformed from the d-form to the l-form, but also deoxygenation at the C(2) position of the sugar was successfully achieved. This is one of the most practical methods for converting a d-sugar to a 2-deoxy-l-sugar in a one-step reaction. To further identify the reaction product, radical reactions followed by treatment with 1,3-propanedithiol and then benzoylation were performed to afford a dithioacetal derivative. The stereochemistry and configuration of the 2-deoxy-l-ribose dithioacetal derivative were confirmed by its X-ray crystal structure. To further apply this methodology, a diethyl thioacetal derivative was formed, followed by selective benzoyl protection, and an NIS-initiated cyclization reaction to give the desired ethyl S-l-2-deoxyriboside, which can be used as a 2-deoxy-l-ribosyl synthon in the formal total synthesis of various l-deoxyribonucleosides, such as l-dT.

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Section: Introductionmentioning

confidence: 99%

Synthesis of l-Deoxyribonucleosides from d-Ribose

2018

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“…Deoxy- l -sugars are involved in a wide range of research areas, ranging from nutritional science to the pharmaceutical industry . They also serve as key building blocks for the preparation of antitumor and antiviral agents, as well as l -DNA and l -nucleosides . Due to their limited availability in nature and an increasing demand in related research, several chemical and biochemical methods for the synthesis of deoxy- l -sugars have been explored.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 3-Deoxy-l-ketohexoses through Group Transfer

Chang

2015

J. Org. Chem.

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A practical method for the synthesis of 3-deoxy-L-ketohexoses is described. Both D- and L-ketohexoses can be transformed into rare 3-deoxy-L-ketohexoses in six steps through a group transfer process. The key step involves a radical cyclized onto a carbonyl group, followed by a fragmentation reaction, eventually resulting in the group transfer of an α-oxy carbonyl group. The process involves tin-free and environmentally benign radical conditions (TTMSS/AIBN/toluene). The acyclic form of 3-deoxy-L-fructose was prepared in only three steps from the inexpensive starting material, D-fructose. A further modification by preparing a dithioacetal derivative was accomplished, which could serve as a convenient sugar synthon for further synthetic applications. Removal of the dithioacetal protecting group results in the formation of the rare 3-deoxy-L-fructose in a total yield of 42%. This methodology could be further extended to the synthesis of other deoxy-L-ketohesoses, such as 3-deoxy-L-sorbose.

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“…Structurally diverse sugar modified nucleosides continue to be investigated for their pharmacological potential, upon which ostensibly minor compositional or configurational alterations may have a substantial impact . The substitution of hydrogen or a hydroxyl group in the furanose ring by fluorine is one such modification which, either alone or in combination with other features, has provided a range of biologically active nucleosides, exemplified by the naturally occurring 4′-fluorinated antibiotic nucleocidin 1 , the 2′-fluorinated antitumor agents gemcitabine 2 and clofarabine 3 and by the first direct acting antiviral approved for the treatment of chronic hepatitis C virus (HCV) infection, sofosbuvir 4 , a monophosphate prodrug of 2′-deoxy-2′-fluoro-2′-methyluridine (Figure A) …”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2,3-Dideoxy-2-fluoro-2,3-endo-methylene- and 2,3-Dideoxy-2-fluoro-3-C-hydroxymethyl-2,3-endo-methylene-pentofuranoses and Their Use in the Preparation of Conformationally Locked Bicyclic Nucleosides

et al. 2015

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Construction of protected 2,3-dideoxy-2-fluoro-2,3-endo-methylene-pentofuranoses from d-glyceraldehyde and 2,3-dideoxy-2-fluoro-3-C-hydroxymethyl-2,3-endo-methylene-pentofuranoses from d-isoascorbic acid, via Simmons-Smith-type stereoselective cyclopropanations on the respective fluoroallyl alcohols, is described. Synthesis of the corresponding conformationally locked sugar modified uridine and guanosine nucleosides was achieved via Vorbrüggen or Mitsunobu methodologies. Stereochemical confirmation of the novel nucleosides was performed on the basis of 2D NOESY NMR experiments. Analysis of 2',3'-dideoxy-2'-fluoro-3'-C-hydroxymethyl-2',3'-endo-methylene-uridine by X-ray crystallography yielded the principal conformational parameters and indicated that the furanoid ring adopted an (o)E/(o)T1, East pucker. The uridine and guanosine nucleosides were found to be inactive in the hepatitis C virus (HCV) cell-based replicon assay, which was corroborated on examination of the corresponding nucleoside triphosphates against the HCV NS5B polymerase.

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L‐Nucleosides

Cited by 5 publications

References 185 publications

Synthesis of l-Deoxyribonucleosides from d-Ribose

Synthesis of l-Deoxyribonucleosides from d-Ribose

Synthesis of 3-Deoxy-l-ketohexoses through Group Transfer

Synthesis of 2,3-Dideoxy-2-fluoro-2,3-endo-methylene- and 2,3-Dideoxy-2-fluoro-3-C-hydroxymethyl-2,3-endo-methylene-pentofuranoses and Their Use in the Preparation of Conformationally Locked Bicyclic Nucleosides

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