Iodoacetoxylation of glycals using cerium(IV) ammonium nitrate, sodium iodide, and acetic acid: stereoselective synthesis of 2-deoxy-2-iodo-alpha-mannopyranosyl acetates.
[formula: see text] The reactions of glycals with ceric(IV) ammonium nitrate and sodium iodide in the presence of acetic acid provides 2-deoxy-2-iodo-alpha-mannopyranosyl acetates with good stereoselectivity. In the majority of the cases examined, the selectivity was considerably better than that from reactions using N-iodosuccinimide and HOAc.
Roush
W R
WR
Department of Chemistry, University of Michigan, Ann Arbor 48109, USA. roush@umich.edu
Narayan
S
S
Bennett
C E
CE
Briner
K
K
D000085:Acetates / Q000138:chemical synthesis* / Q000737:chemistry; D002563:Cerium / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry*; D012974:Sodium Iodide / Q000737:chemistry*
D000085:Acetates; D002563:Cerium; D012974:Sodium Iodide; D005947:Glucose; D008358:Mannose; C004653:ceric ammonium nitrate