Synthesis of 4-Thio-D- and -L-ribofuranose and the Corresponding Adenine Nucleosides

Reist, Elmer J.; Gueffroy, Donald E.; Goodman, Leon

doi:10.1021/ja01078a050

Cited by 109 publications

(57 citation statements)

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“…Thianucleosides in which the oxygen atom of the furanose ring has been replaced by a sulfur atom were first synthesized in 1964 (72). Some showed interesting biological activities such as inhibition of S-adenosylhomocysteine hydrolase (52).…”

Section: Thia Analogs Of Ddns and Isoddnsmentioning

confidence: 99%

Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry

Nair

Jahnke

1995

Antimicrob Agents Chemother

145

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In summary, many isomeric analogs of ddNs of both D-related and L-related absolute stereochemistries have been synthesized and evaluated in vitro for their antiviral activities. A few of these compounds exhibit potent antiviral activity and, interestingly, belong to both the D and L families. The synthetic methodologies developed will allow accessibility to many more novel modified nucleosides. While some structure-activity relationships are emerging from this work, it is clear that these chiral isomeric nucleosides have opened a new chapter in the field of antiviral nucleosides.

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Section: Thia Analogs Of Ddns and Isoddnsmentioning

confidence: 99%

Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry

Nair

Jahnke

1995

Antimicrob Agents Chemother

145

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“…The easy C-2 inversion of D-ribose in an acetolyzing medium appeared to be inconsistent with the results of Reist et al who acetolyzed 4-S-benzoyl-4-thioribopyranose derivatives to 4-thio-ribofuranose compounds without epimerization of the latter (18). When their experimental conditions were used with D-ribose, the starting material was recovered accompanied by only a trace of D-arabinose detectable by paper chromatography.…”

Section: Introductionmentioning

confidence: 65%

“…The acetolysis conditions used by Reist et al (18) for converting 4-S-benzoyl-4-thio-ribopyranosides to 4-thioribofuranose derivatives without observable C-2 epimerization were applied to D-ribose. To an ice-cold solution of acetic acid (38 ml), acetic anhydride (38 rill), and sulfuric acid (2.3 ml) was added 0.9 g (0.06 mol) of D-ribose.…”

Section: Non-epitnerization Of D-ribose In An Acetolysis Mixturementioning

confidence: 99%

Epimerization of Monosaccharides Under Acetolysis Conditions

Sowa¹

1971

Can. J. Chem.

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Monosaccharides with a cis-configuration at C-2 and -3 readily undergo inversion at C-2 in an acetolysis medium composed of acetic acid, acetic anhydride, and sulfuric acid. The acetolysis-inversion reaction has been carried out with 2,3;5,6-di-0-isopropylidene-D-gulofuranose, 2,3;6,7-di-0-isopropylidene-D-glycero-D-gulo-heptose, 2,3-0-isopropylidene-D-ribose, D-ribose, and D-mannose using chromatography for isolation of the deacetylated epimeric products. The reaction requires a medium with a high concentration of acetic acid (ca. 90%) and appears to take place only with furanose structures. Inversions observed with the unsubstituted pyranoses D-ribose and D-mannose probably occur because of tautomerization to furanose forms. The epimerization proceeds in the direction which yields a smaller number of cis-oriented groups at C-2, -3, and -4 of the furanose forms of monosaccharides.

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“…To our knowledge, at the time that we began this project, the only 4′-thionucleosides that had been synthesized were 4′-thioribonucleosides, [17][18][19] 4′-thioarabinonucleosides [20][21][22] and 2′-deoxy-4′-thionucleosdes. 13,14) The development of a synthetic strategy for 4′-thionucleosides applicable to the synthesis of 2′-substituted derivatives was thus a key to the success of this project.…”

Section: Development Of Pummerer-type Glycosylation and Its Applicatimentioning

confidence: 99%

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

Yoshimura

Saito

Natori

et al. 2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Many attempts have been made to synthesize structurally novel nucleoside derivatives in order to identify effective compounds for the treatment of tumors and virus-caused disease. At our laboratories, as part of our efforts to synthesize 4′-thionucleosides, we have identified and characterized biologically active nucleosides. During the course of our synthetic study, we developed the Pummerer-type thioglycosylation reaction. As a result, we synthesized a potent antineoplastic nucleoside, 1-(2-deoxy-2-fluoro-β-D-4-thio-arabinofuranosyl)cytosine (4′-thioFAC), and several novel 4′-thionucleosides that possess antiherpes virus activities.

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Synthesis of 4-Thio-D- and -L-ribofuranose and the Corresponding Adenine Nucleosides

Cited by 109 publications

References 0 publications

Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry

Antiviral activities of isometric dideoxynucleosides of D- and L-related stereochemistry

Epimerization of Monosaccharides Under Acetolysis Conditions

Synthesis of 4′-Thionucleosides as Antitumor and Antiviral Agents

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