Zinnchlorid‐katalysierte Ribosidierung von Triazoloinosin | Zendy

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Zinnchlorid‐katalysierte Ribosidierung von Triazoloinosin

Author(s) -

Schlimme Eckhard

Publication year - 1981

Publication title -

liebigs annalen der chemie

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 0170-2041

DOI - 10.1002/jlac.198119811020

Subject(s) - chemistry , tin , acetonitrile , chloride , medicinal chemistry , acetyl chloride , condensation , catalysis , stereochemistry , organic chemistry , physics , thermodynamics

Tin Chloride‐catalyzed Ribosidation of Triazoloinosine Condensation of 3‐(β‐D‐ribofuranosyl)‐9‐(trimethylsiloxy)‐3 H ‐ s ‐triazolo[2,3‐ a ]purine ( 3 ) with 1,2,3,5‐tetra‐ O ‐acetyl‐β‐D‐ribofuranose in acetonitrile in the presence of tin chloride is regio‐selective and yields after deacylation 3,5‐dihydro‐3,5‐bis(β‐D‐ribofuranosyl)‐9 H ‐ s ‐triazolo[2,3‐ a ]‐purin‐9‐one ( 5 ). The assignment of the ribosidation site in 5 is based upon carbon‐13 chemical shifts observed in the nucleosides 5 and 1 when compared to the anionic form 7 .

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