87119-52-6Relevant academic research and scientific papers
Glycosylimidates, 8. - Synthesis of 1-Thioglycosides
Schmidt, Richard R.,Stumpp, Michael
, p. 1249 - 1256 (2007/10/02)
As expected, the reactive acetyl-protected O-(α-D-glucopyranosyl) trichloroacetimidate 3 reacts with S-nucleophiles and trifluoroborane-ether as catalyst to yield exclusively 1-thio-β-D-glucopyranosides with inversion of the configuration.The corresponding benzyl-protected α-trichloroacetimidate 4 affords with retention of the configuration alkyl 1-thio-α-D-glucopyranosides.The importance of alkyl 1-thio-β-D-galactopyranosides in enzyme induction was reason to apply this convenient and efficient glycosyl-transfer reaction to the synthesis of isopropyl 1-thio-β-D-galactopyranoside (12a) and the sodium salt of 1-thio-β-D-galactopyranose (12b), respectively.
