Abstract
The synthesis of oligosaccharide mimics incorporating a thiourea intersaccharide bridge by coupling of mono- and disaccharide per- O-acetylated glycosyl isothiocyanates and methyl 6-amino-6-deoxy-α- d-glucopyranoside, is reported. An unexpected anomerization reaction was observed, however, for α- and β- d-mannopyranosylthioureido derivatives upon Zemplén deacetylation. Kinetics studies revealed that this anomerization process is base catalysed and strongly dependent upon reaction temperature and reaction time. The fully unprotected compounds could be obtained without epimerization by performing the last step at 0 °C. In all cases, the final pseudooligosaccharides were stable in water solution at room temperature in the absence of base.
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Disclaimer: All third-party content on this website/platform is and will remain the property of their respective owners and is provided on "as is" basis without any warranties, express or implied. Use of third-party content does not indicate any affiliation, sponsorship with or endorsement by them. Any references to third-party content is to identify the corresponding services and shall be considered fair use under The CopyrightLaw.