Nucleoside Syntheses, XXI. Synthesis of 5-Methylaminomethyl-2-thiouridine, a Rare Nucleoside from t-RNA

✍ Scribed by Vorbrüggen, Helmut ;Krolikiewicz, Konrad

• Publisher: John Wiley and Sons
• Year: 1980
• Tongue: English
• Weight: 584 KB
• Volume: 1980
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.198019800913

✦ Synopsis

Abstract

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.