New synthesis of both D- and L-3-O-carbamoyl-2-deoxy-4-thioribosides, substrates for β-selective glycosylations

Shaw‐Ponter, S.; Rider, Peter; Young, Robert J.

doi:10.1016/0040-4039(96)00139-6

Cited by 6 publications

(1 citation statement)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Recently (Dyson et al, 1991a), an efficient synthesis of benzyl 3,5-di-Q-benzyl-2-deoxy-1-thio-o-erythro-pentofuranoside which could be used in the synthesis of 4"-thlo-z -deoxynucleoside analogues was described. Other suitable sugar syntheses have since been reported by others (Uenishi et al, 1991;Shaw-Ponter et al, 1996). Many 4'-thio-2'-deoxynucleoside analogues have since been synthesized (Dyson et al, 1991b;Secrist et al, 1991;Walker et al, 1994;Rahim et al, 1996) and in particular, several such pyrimidine nucleoside analogues have been shown to possess significant antiviral (usually antiherpesvirus) activity (Dyson et al, 1991b;Walker et el., 1994;Rahim et al, 1996).…”

Section: Introductionmentioning

confidence: 99%

4′-Thio-5-Ethyl-2′-Deoxyuridine5′-Triphosphate (TEDUTP): Synthesis and Substrate Properties in DNA-Synthesizing Systems

Alexandrova

Semizarov

Krayevsky

et al. 1996

Antivir Chem Chemother

View full text Add to dashboard Cite

SummaryAn efficient synthesis of the 5'-phosphate and 5'-triphosphate of a 4'-thio-2'-deoxynucleoside is described for the first time. The 5'-triphosphate of the antiherpesvirus agent 4'-thio-5-ethyl-2'-deoxyuridine (TEDU) has been shown to be a good substrate for human placental DNA polymerase ex, calf thymus terminal deoxynucleotidyl transferase, and the reverse transcriptases of human immunodeficiency virus and avian myeloblastosis virus. As it is known that TEDU is a substrate only for herpesvirus-encoded thymidine kinases and not the cellular kinases, it is likely that the utilization of TEDUTP by DNA-synthesizing enzymes results in the selective toxicity seen in vitro in herpesvirus-infected cells.

show abstract

Section: Introductionmentioning

confidence: 99%

4′-Thio-5-Ethyl-2′-Deoxyuridine5′-Triphosphate (TEDUTP): Synthesis and Substrate Properties in DNA-Synthesizing Systems

Alexandrova

Semizarov

Krayevsky

et al. 1996

Antivir Chem Chemother

View full text Add to dashboard Cite

show abstract

ChemInform Abstract: New Synthesis of Both D‐ and L‐3‐O‐Carbamoyl‐2‐deoxy‐4‐thioribosides, Substrates for β‐Selective Glycosylations.

1996

View full text Add to dashboard Cite

show abstract

Stereoselective synthesis and conformational analysis of aromatic C‐thionucleosides

Juarez

García

Hommer

et al. 2006

Heteroatom Chemistry

View full text Add to dashboard Cite

Tetrahydrothiophene derivatives 2a–2d, which are useful intermediates in the synthesis of C‐thionucleosides, were obtained by a tandem strategy that involves the base‐catalyzed conjugate addition of ethyl 2‐mercaptoacetate to trans‐cinnamaldehyde followed by cyclization. The solvent and the nature of the amine used as Lewis base influence the stereo‐ selectivity of the reaction. The reduction of each isolated derivative 2a–2d was performed with LiAlH4 to afford C‐thionucleosides 3a–3d. The configuration and conformation of each diastereomer 2a–2d and 3a–3d was assigned by means of the analysis of vicinal proton–proton coupling constants. The X‐ray structure of 2d, 3a, and 3b confirmed the configuration assigned to each isomeric tetrahydrothiophenes. © 2006 Wiley Periodicals, Inc. Heteroatom Chem 17:289–298, 2006; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20205

show abstract

New synthesis of both D- and L-3-O-carbamoyl-2-deoxy-4-thioribosides, substrates for β-selective glycosylations

Cited by 6 publications

References 11 publications

4′-Thio-5-Ethyl-2′-Deoxyuridine5′-Triphosphate (TEDUTP): Synthesis and Substrate Properties in DNA-Synthesizing Systems

4′-Thio-5-Ethyl-2′-Deoxyuridine5′-Triphosphate (TEDUTP): Synthesis and Substrate Properties in DNA-Synthesizing Systems

ChemInform Abstract: New Synthesis of Both D‐ and L‐3‐O‐Carbamoyl‐2‐deoxy‐4‐thioribosides, Substrates for β‐Selective Glycosylations.

Stereoselective synthesis and conformational analysis of aromatic C‐thionucleosides

Contact Info

Product

Resources

About