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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 .