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Indoxylic Acid Esters as Convenient Intermediates Towards Indoxyl Glycosides
Author(s) -
Böttcher Stephan,
Thiem Joachim
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301198
Subject(s) - chemistry , glycoside , glycosylation , glycosyl , decarboxylation , halide , acetylation , organic chemistry , combinatorial chemistry , catalysis , biochemistry , gene
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 Zemplén 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.