Synthesis of aryl D-gluco- and D-galacto-pyranosides and 1-O-acyl-D-gluco- and -D-galacto-pyranoses exploiting the Mitsunobu reaction. Influence of the pKa of the acid on the stereoselectivity of the reaction.
Glycosides (alpha- and beta-D-glucosides and -D-galactosides) derived from three pesticides, 2-tert-butyl-2,4-dinitrophenol,2,6-dibromo-4-cyanophenol, and 5-(2,4-dichlorophenoxy)-2-nitrobenzoic acid, were synthesized from 2,3,4,6-tetra-O-chloroacetyl-D-gluco- and -D-galactopyranose by use of the Mitsunobu reaction. It was shown that selectivity for the beta-D anomer increases with the pKa of the acid component.
Lubineau
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A
Laboratoire de Chimie Organique Multifonctionnelle (U.R.A. C.N.R.S. 462), Institut de Chimie Moléculaire d'Orsay, Université de Paris-Sud, France.
Meyer
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E
Place
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P
D004140:Dinitrophenols / Q000737:chemistry; D005697:Galactosides / Q000138:chemical synthesis*; D005960:Glucosides / Q000138:chemical synthesis*; D006540:Herbicides / Q000737:chemistry*; D007536:Isomerism; D009570:Nitriles / Q000737:chemistry; D010647:Phenyl Ethers / Q000737:chemistry
D004140:Dinitrophenols; D005697:Galactosides; D005960:Glucosides; D006540:Herbicides; D009570:Nitriles; D010647:Phenyl Ethers; C010937:dinoterb; C006826:bromoxynil; C050421:bifenox