Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 18, Pages 4000-4005Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500137
Keywords
Synthetic methods; Homogeneous catalysis; Gold; Glycosylation; Glycosides; Carbohydrates; Amino acids
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Funding
- Department of Science and Technology (DST), New Delhi [JCB/SR/S2/JCB-26/2010]
- Council of Scientific and Industrial Research (CSIR), New Delhi [02(0124)/13/EMR-II]
- University Grants Commission (UGC), New Delhi
- CSIR
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Glycosylations of armed and disarmed trichloroacetimidate-based glycosyl donors were carried out by using the AuCl3-phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5-45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2-O-acetyl-protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid-sensitive nucleophiles such as Fmoc-serine tert-butyl ester or Fmoc-threonine tert-butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.
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