Affiliation:
1. Department of Chemistry National Institute of Technology Patna 800 005 Patna India
2. Department of Chemistry Indian Institute of Technology Patna 801 106 Patna India
Abstract
AbstractStereoselective construction of glycosidic linkages have emerged as one of the pivotal aspects for the synthesis of complex oligosaccharide assemblies. We herein report C2‐cyanomethyl (CNMe) ether as a strong stereodirecting group on trichloroacetimidate glycosyl donors for the synthesis of 1,2‐trans‐β‐O‐glycosides. The developed donors bearing various arming and disarming protections along with C2‐CNMe ether delivered the glycosides in short reaction time, moderate to good yields and high to excellent stereoselectivities.Gluco‐ andgalacto‐ configured donors were found compatible with an array of alcohols having varied reactivities. The orthogonality of the CNMe ether protection with silyl ether group has been further explored for sequential glycosylations.
Funder
National Institute of Technology, Patna
Subject
Organic Chemistry,Physical and Theoretical Chemistry
Cited by
2 articles.
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