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Nucleoside Syntheses, XXI. Synthesis of 5‐Methylaminomethyl‐2‐thiouridine, a Rare Nucleoside from t‐RNA
Author(s) -
Vorbrüggen Helmut,
Krolikiewicz Konrad
Publication year - 1980
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.198019800913
Subject(s) - chemistry , nucleoside , silylation , moiety , trimethylsilyl , nucleic acid , perchlorate , combinatorial chemistry , stereochemistry , organic chemistry , catalysis , biochemistry , ion
The synthesis of 5‐methylaminomethyl‐2‐thiouridine (1) , a rare nucleoside from t‐RNA, starting from the appropriate 2‐thiouracil and ribose derivatives is described. During the silyl Hilbert‐Johnson nucleoside synthesis with silver perchlorate the tert ‐butoxycarbonyl (Boc) aminoprotecting group in the 2‐thiouracil moiety is removed. This cleavage is due to the intermediate formation of trimethylsilyl perchlorate. Preparative applications of this new type of Lewis acids are mentioned.