137407-83-1Relevant academic research and scientific papers
UNIQUE 1'-O-BOC PROTECTION OF VIRGINIAMYCIN S AND RESULTING RESISTANCE AGAINST SODIUM HYDROXIDE
Moerman, Marc C.,Anteunis, Marc J. O.
, p. 647 - 652 (2007/10/02)
The picolinic hydroxyl in Virginiamycin S1 (VS%1; 1a) can be protected with di-tert-butyloxycarbonate affording the tert-butyloxycarbonyl derivative thus yielding VS1-1'-O-Boc (1b) in a fast and quantitative conversion without concomitant betaine (1c) formation.Once protected however, the lactone bond in 1b can no longer be cleaved under mild alkaline conditions.A possible explanation is given.
