Unprecedented Transformation of Thioglycosides to Their Corresponding 1‐O‐Acetates in the Presence of HClO₄‐SiO₂§

^§C.D.R.I. communication no. 6979.

Abstract

An unprecedented conversion of thioalkyl/aryl glycoside to the corresponding 1‐O‐acetates has been described using acetic anhydride and HClO₄‐SiO₂ at rt. Although this transformation does not play an important role in the oligosaccharide synthesis in comparison to its reverse transformation, this gives useful information in selecting the reaction condition for the synthesis of oligosaccharides. The yields were excellent in all cases.

^§C.D.R.I. communication no. 6979.

Keywords:

• Carbohydrate
• Thioglycosides
• Acetates
• One‐pot
• HClO₄‐SiO₂

Acknowledgements

Instrumentation facilities from SAIF, CDRI are gratefully acknowledged. G.A. and P.T. thank CSIR, New Delhi, for providing Senior Research Fellowships. This project was partly funded by Department of Science and Technology (DST), New Delhi (SR/FTP/CSA‐10/2002), India.

Notes

^§C.D.R.I. communication no. 6979.

Additional information

Notes on contributors

Geetanjali Agnihotri

Authors contributed equally to this work.

Pallavi Tiwari

Authors contributed equally to this work.

Anup Kumar Misra

Authors contributed equally to this work.