Glucuronidation of alcohols using the bromosugar-iodonium reagent method

The glycosidation method introduced by Field, employing bromosugars as donors in conjunction with iodine, has been evaluated for glucuronidation. Despite the low donor ability of glucuronates, beta -glucuronides were obtained in 70-85% yield from a number of primary alcohols, and in 50-65% from two secondary alcohols, using the pivaloyl compound 11 with NIS as promoter. By contrast, the use of IBr or ICI as promoter gave mainly the alpha -glucuronides. (C) 2001 Elsevier Science Ltd. All rights reserved.