A Concise Route To Water-Soluble 2,6-Disubstituted Bodipy-Carbohydrate Fluorophores By Direct Ferrier-Type C-Glycosylation
JOURNAL OF ORGANIC CHEMISTRY(2021)
摘要
Novel, linker-free, BODIPY-carbohydrate derivatives containing sugar residues at positions C2 and C6 are efficiently obtained by, hitherto unreported, Ferrier-type C-glycosylation of 8-aryl-1,3,5,7-tetramethyl BODIPYs with commercially available tri-O-acetyl-D-glucal followed by saponification. This transformation, which involves the electrophilic aromatic substitution (SEAr) of the dipyrrin framework with an allylic oxocarbenium ion, provides easy access to BODIPY-carbohydrate hybrids with excellent photophysical properties and a weaker tendency to aggregate in concentrated water solutions.
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关键词
water-soluble,bodipy-carbohydrate,ferrier-type,c-glycosylation
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