Glycosidation with a disarmed glycosyl iodide: promotion and scope.
[reaction: see text] Glucuronyl iodide 1 has been studied in detail as a "disarmed" glycosyl donor. In a model reaction, using N-iodosuccinimide (NIS) as a promoter and 2-phenylethanol as acceptor, best results were obtained using NIS with I(2), followed by trimethylsilyltrifluoromethanesulfonate (TMSOTf). When a series of primary and secondary alcohols was glycosylated using these conditions, yields of 60-83% of beta-glucuronides were obtained. Various "nonheavy" metal salts also effectively catalyzed the model reaction but led to significant amounts of alpha-product with less reactive secondary alcohols.
Perrie
Jennifer A
JA
The Robert Robinson Laboratories, Department of Chemistry, University of Liverpool, Liverpool L 69 7 ZD, UK.
Harding
John R
JR
King
Clare
C
Sinnott
Deborah
D
Stachulski
Andrew V
AV
D000438:Alcohols / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D005965:Glucuronates / Q000737:chemistry*; D006027:Glycosides / Q000378:metabolism; D006031:Glycosylation; D015394:Molecular Structure; D010626:Phenylethyl Alcohol / Q000737:chemistry; D013388:Succinimides / Q000737:chemistry
D000438:Alcohols; D004952:Esters; D005965:Glucuronates; D006027:Glycosides; D013388:Succinimides; C485386:methyl 1-deoxy-1-iodo-O(2),O(3),O(4)-triacetylglucuronate; C008155:N-iodosuccinimide; D010626:Phenylethyl Alcohol