Beilstein J. Org. Chem.2016,12, 524–530, doi:10.3762/bjoc.12.51
to the stereoselective glycoside synthesis. The final products were obtained by conventional Zemplén deacetylation.
Keywords: diastereoselectivity; p-hydroxyphenylalkylglycosides; mild promoters; natural products; 1,2-trans-glycosylation; Introduction
Arylalkyl (substituted benzyl, phenethyl and
glycosides 1–3, 31a,b and 32–37 were isolated in high yields (Figure 3).
Conclusion
The glycosylation methods studied in this work represent a simple and convenient approach to bioactive natural p-hydroxyphenylalkylglycosides and their analogues. The mild reaction conditions with exclusive stereoselectivity
the synthesis of p-hydroxyphenylalkylglycosides.
Synthesis of 21a–c to 30 under various conditions.
Supporting Information
Supporting Information File 44: Experimental procedures and analytical data.
Acknowledgements
This work was supported by the Slovak Research and Development Agency under the
PDF
Graphical Abstract
Figure 1:
Structures of vanillyl β-D-glucoside (1), salidroside (2) and isoconiferin (3).