OFox imidates as versatile glycosyl donors for chemical glycosylation.
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.
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Swati S
SS
Nigudkar
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Tinghua
T
Wang
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Salvatore G
SG
Pistorio
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Jagodige P
JP
Yasomanee
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Keith J
KJ
Stine
Department of Chemistry and Biochemistry, University of Missouri - St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu.
Alexei V
AV
Demchenko
D006031:Glycosylation; D007096:Imidoesters / Q000138:chemical synthesis / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D007096:Imidoesters; D007211:Indoles