Premium
Nucleoside syntheses, XXII 1) Nucleoside synthesis with trimethylsilyl triflate and perchlorate as catalysts
Author(s) -
Vorbrüggen Helmut,
Krolikiewicz Konrad,
Bennua Bärbel
Publication year - 1981
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19811140404
Subject(s) - chemistry , nucleoside , lewis acids and bases , catalysis , trifluoromethanesulfonate , trimethylsilyl , trimethylsilyl trifluoromethanesulfonate , organic chemistry , medicinal chemistry , stereochemistry
The novel Lewis acids (CH 3 ) 3 SiOSO 2 CF 3 ( 3 ), (CH 3 ) 5 SiOSO 2 C 4 F 9 ( 6 ), and (CH 3 ) 3 SiClO 4 ( 4 ) are highly selective and efficient Friedel‐Crafts catalysts for nucleoside formation form silylated heterocycles and peracylated sugars as well as for rearrangements of persilylated protected nucleosides. With basic silylated heterocycles these new catalysts give much higher yields of the natural N ‐1‐nucleosides than with SnCl 4 .