Facile oxidative cleavage of 4-O-benzyl ethers with dichlorodicyanoquinone in rhamno- and mannopyranosides.
On exposure to dichlorodicyanoquinone in wet dichloromethane at room temperature, equatorial 4-O-benzyl ethers are removed with moderate selectivity in the presence of other benzyl ethers in glycopyranosides and glycothiopyranosides.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Vinogradova
Olga
O
D001593:Benzyl Compounds / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D004987:Ethers / Q000737:chemistry; D005663:Furans / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D010084:Oxidation-Reduction; D011809:Quinones / Q000737:chemistry*; D012210:Rhamnose / Q000737:chemistry*
D001593:Benzyl Compounds; D004987:Ethers; D005663:Furans; D011809:Quinones; C520778:dichlorodicyanoquinone; D008358:Mannose; D012210:Rhamnose