Literature DB >> 27808325

OFox imidates as versatile glycosyl donors for chemical glycosylation.

Swati S Nigudkar1, Tinghua Wang1, Salvatore G Pistorio1, Jagodige P Yasomanee1, Keith J Stine1, Alexei V Demchenko1.   

Abstract

Previously we communicated 3,3-difluoroxindole (HOFox) - mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study with the main focus on the synthesis of various OFox imidates and their investigation as glycosyl donors for chemical 1,2-cis and 1,2-trans glycosylation.

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Year:  2017        PMID： 27808325      PMCID： PMC5499515          DOI： 10.1039/c6ob02230h

Source DB:  PubMed          Journal:  Org Biomol Chem        ISSN： 1477-0520            Impact factor:   3.876


  26 in total

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10.  Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry.

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Review 6.  Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century.

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Review 7.  Recent Advances in Stereoselective Chemical O-Glycosylation Reactions.

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8.  A Streamlined Regenerative Glycosylation Reaction: Direct, Acid-Free Activation of Thioglycosides.

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  8 in total

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