Nucleoside von fluor-zuckern
2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establ...
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| Autor*in: |
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| Format: |
E-Artikel |
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| Sprache: |
Deutsch |
| Erschienen: |
1970 |
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| Reproduktion: |
Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 |
|---|---|
| Übergeordnetes Werk: |
in: Carbohydrate Research - Amsterdam : Elsevier, 12(1970), 3, Seite 301-311 |
| Übergeordnetes Werk: |
volume:12 ; year:1970 ; number:3 ; pages:301-311 |
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| 520 | |a 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. | ||
| 520 | |a Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. | ||
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| 700 | 1 | |a Langen, P. |4 oth | |
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(DE-627)NLEJ175424047 (DE-599)GBVNLZ175424047 DE-627 ger DE-627 rakwb ger Nucleoside von fluor-zuckern 1970 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Kowollik, G. oth Gaertner, K. oth Etzold, G. oth Langen, P. oth in Carbohydrate Research Amsterdam : Elsevier 12(1970), 3, Seite 301-311 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:12 year:1970 number:3 pages:301-311 http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80612-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 12 1970 3 301-311 |
| spelling |
(DE-627)NLEJ175424047 (DE-599)GBVNLZ175424047 DE-627 ger DE-627 rakwb ger Nucleoside von fluor-zuckern 1970 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Kowollik, G. oth Gaertner, K. oth Etzold, G. oth Langen, P. oth in Carbohydrate Research Amsterdam : Elsevier 12(1970), 3, Seite 301-311 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:12 year:1970 number:3 pages:301-311 http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80612-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 12 1970 3 301-311 |
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(DE-627)NLEJ175424047 (DE-599)GBVNLZ175424047 DE-627 ger DE-627 rakwb ger Nucleoside von fluor-zuckern 1970 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Kowollik, G. oth Gaertner, K. oth Etzold, G. oth Langen, P. oth in Carbohydrate Research Amsterdam : Elsevier 12(1970), 3, Seite 301-311 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:12 year:1970 number:3 pages:301-311 http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80612-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 12 1970 3 301-311 |
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(DE-627)NLEJ175424047 (DE-599)GBVNLZ175424047 DE-627 ger DE-627 rakwb ger Nucleoside von fluor-zuckern 1970 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Kowollik, G. oth Gaertner, K. oth Etzold, G. oth Langen, P. oth in Carbohydrate Research Amsterdam : Elsevier 12(1970), 3, Seite 301-311 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:12 year:1970 number:3 pages:301-311 http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80612-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 12 1970 3 301-311 |
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(DE-627)NLEJ175424047 (DE-599)GBVNLZ175424047 DE-627 ger DE-627 rakwb ger Nucleoside von fluor-zuckern 1970 nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier 2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. Elsevier Journal Backfiles on ScienceDirect 1907 - 2002 Kowollik, G. oth Gaertner, K. oth Etzold, G. oth Langen, P. oth in Carbohydrate Research Amsterdam : Elsevier 12(1970), 3, Seite 301-311 (DE-627)NLEJ175413258 (DE-600)1496822-8 0008-6215 nnns volume:12 year:1970 number:3 pages:301-311 http://linkinghub.elsevier.com/retrieve/pii/S0008-6215(00)80612-6 GBV_USEFLAG_H ZDB-1-SDJ GBV_NL_ARTICLE AR 12 1970 3 301-311 |
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| abstract |
2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. |
| abstractGer |
2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. |
| abstract_unstemmed |
2',5'-Dideoxy-5'-fluororibonucleosides are conveniently obtained by treatment of the corresponding 5'-O-tosyl1Tosyl = p-toluenesulfonyl. derivatives with an excess of tetrabutylammonium fluoride in N,N-dimethylformamide at 50^o. The p.m.r. spectra of the fluoro derivatives establish unequivocally their structure. Surprisingly, treatment of 3',5'-di-O-mesylthymidine with potassium fluoride or with tetrabutylammonium fluoride gave mesylanhydrothymidines rather than fluorine-containing products. Under similar conditions, 5'-deoxy-5'-iodothymidine was converted mainly into 4',5'-unsaturated 5'-deoxythymidine. Es wird gezeigt, dasz 2',5'-Didesoxy-5'-fluorribonucleoside in einfacher Weise aus den entsprechenden 5'-O-tosylierten Derivaten durch Umsatz mit Tetrabutylammoniumfluorid in N,N-Dimethylformamid bei 50^o erhalten werden. Die p.m.r.-Spektren der Fluor-Derivative erweisen einwandfrei deren Struktur. Uberraschenderweise bildet 3',5'-Di-O-mesylthymidin mit Kaliumfluorid oder mit Tetrabutylammoniumfluorid kein fluorhaltiges Produkt, sondern mesylierte Anhydrothymidine. Aus 5'-Desoxy-5'-jodthymidin entsteht unter ahnlichen Bedingungen vorwiegend 5'-Desoxy-4',5'-didehydrothymidin. |
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Nucleoside von fluor-zuckern |
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