Regioselective C-3-O-acylation and O-methylation of 4,6-O-benzylidene-beta-D-gluco- and galactopyranosides displaying a range of anomeric substituents.
The regioselective C-3-O-acylation and O-methylation of a range of 4,6-O-benzylidene-beta-D-gluco- and galactopyranosides has been studied. Regioselectivity is achieved by forming the copper chelate of the 2,3-diol using either sodium hydride and copper(II) chloride, or copper(II) acetylacetanoate, or copper(II) acetate, prior to introduction of the acylating or methylating agent.
Osborn
H M
HM
Department of Chemistry, University of Reading, Whiteknights, UK. h.m.i.osborn@reading.ac.uk
Brome
V A
VA
Harwood
L M
LM
Suthers
W G
WG
D000215:Acylation; D000478:Alkylation; D002614:Chelating Agents / Q000737:chemistry; D002855:Chromatography, Thin Layer; D003300:Copper / Q000737:chemistry; D005690:Galactose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005947:Glucose / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008745:Methylation; D019906:Nuclear Magnetic Resonance, Biomolecular; D009942:Organometallic Compounds / Q000737:chemistry; D013329:Structure-Activity Relationship
C438444:4,6-O-benzylidene-D-glucopyranose; D002614:Chelating Agents; D009942:Organometallic Compounds; C440772:copper(II) acetylacetanoate; C015092:cupric acetate; D003300:Copper; D005947:Glucose; C029892:cupric chloride; D005690:Galactose