1607828-46-5Relevant articles and documents
Indoxylic acid esters as convenient intermediates towards indoxyl glycosides
Boettcher, Stephan,Thiem, Joachim
, p. 564 - 574 (2014)
Indoxylic acid methyl and allyl esters with varied halide-substitution patterns were obtained in excellent yields using a scalable route. Phase-transfer glycosylation of these key intermediates was carried out with various glycosyl halides. Subsequent mild silver-mediated decarboxylation followed by Zemplen deacetylation led to indoxyl glycosides in good overall yields. Indoxyl glycosides are well-established and widely used tools for enzyme screening and enzyme-activity monitoring. In the past, their synthesis has been difficult, so this new approach has led to a variety of useful structures. Indoxyl glycosides with varied halide-substitution patterns were synthesized using indoxylic acid esters as key intermediates. Glycosylation under phase-transfer conditions, ester cleavage, and mild decarboxylation led to the indoxyl glycosides in good yields. This approach enables access to a number of different indoxyl compounds. Copyright
