Allyl deprotection of galacturonic acid derivatives: mechanistic aspects of mercuric-catalyzed prop-1-enyl acetal cleavage.
Different deallylation methods were assayed for selective deprotection of allyl galactopyranosiduronic acid derivatives. A two-step procedure using DABCO and (Ph(3)P)(3)RhCl followed by mercuric-assisted cleavage gave quantitative yields. Reaction in the presence of [(18)O]water allowed us to obtain evidence about the mechanism of prop-1-enyl cleavage.
Barbier
Maximilien
M
Laboratoire des Glucides UMR CNRS 6219, Université de Picardie Jules Verne, 33 Rue Saint-Leu, 80039 Amiens, France.
Grand
Eric
E
Kovensky
José
J
D000080:Acetals / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry*; D006603:Hexuronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008628:Mercury / Q000494:pharmacology*; D008956:Models, Chemical; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry; D012238:Rhodium / Q000737:chemistry*; D013696:Temperature; D014867:Water / Q000737:chemistry
D000080:Acetals; D002241:Carbohydrates; D006603:Hexuronic Acids; D010879:Piperazines; D014867:Water; C007819:galacturonic acid; D012238:Rhodium; D008628:Mercury; C007306:triethylenediamine