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Synthesis of the β‐D‐Glucuronides of 2,3‐, 3,4‐, and 2,6‐Dichlorophenol
Author(s) -
Goenechea Sabino,
Rücker Gerhard,
Hubert Marcus A.
Publication year - 2001
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/1521-4184(200103)334:3<101::aid-ardp101>3.0.co;2-2
Subject(s) - glucuronate , chemistry , glucuronide , glucuronates , hydrolysis , alkaline hydrolysis , cleavage (geology) , 2,4 dichlorophenol , stereochemistry , organic chemistry , glucuronic acid , metabolism , biochemistry , polysaccharide , geotechnical engineering , fracture (geology) , biology , bacteria , genetics , engineering
The β‐D‐glucuronides of 2,3‐, 3,4‐, and 2,6‐dichlorophenol ( 1 — 3 ) were prepared by a modified Koenigs‐Knorr synthesis. As the alkaline hydrolysis of perpivaloylated methyl (2,3‐dichlorophenyl)‐ glucuronate 1a led to a dehydrated glucuronide, the preparation of peracetylated methyl dichlorophenylglucuronates with subsequent cleavage of the ester bindings under mild conditions was preferred.