Indium triflate catalyzed peracetylation of carbohydrates.
Peracetylation is a very common protection strategy that is widely implemented in carbohydrate synthesis. Here, a method for the peracetylation of carbohydrates using catalytic In(OTf)(3) in neat acetic anhydride is reported. In(OTf)(3) has low toxicity and is mild and water tolerant, and the reactions are high yielding and efficient. Details regarding the scope and mechanism of the reaction are briefly discussed.
Bizier
Nicholas P
NP
Department of Chemistry and Biochemistry, Montana State University, Bozeman, MT 59717, USA.
Atkins
Shannon R
SR
Helland
Luke C
LC
Colvin
Shane F
SF
Twitchell
Joseph R
JR
Cloninger
Mary J
MJ
D000107:Acetylation; D002241:Carbohydrates / Q000737:chemistry* / Q000528:radiation effects; D002384:Catalysis; D007204:Indium / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D008872:Microwaves; D012995:Solubility
D002241:Carbohydrates; D008698:Mesylates; D007204:Indium; C012077:trifluoromethanesulfonic acid