Syntheses of all the possible monomethyl ethers and several deoxyhalo analogues of methyl beta-lactoside as ligands for the Ricinus communis lectins.
The synthesis of all the possible monomethyl ethers of methyl beta-lactoside (1) has been performed from 1 in a straightforward way, making use of the different reactivity of the hydroxyl groups in alkylation and stannylation reactions. In addition, the deoxyfluoro derivatives of 1 at positions, 6,3',4',epi-4', and 6' have been prepared by reaction of the appropriate substrates with diethylaminosulfur trifluoride or tetrabutylammonium fluoride. Finally, the 6-deoxyiodo and 6'-bromodeoxy analogues of 1 have also been prepared.
Fernández
P
P
Grupo de Carbohidratos, Instituto de Química Orgánica, C.S.I.C., Madrid, Spain.
Jiménez-Barbero
J
J
Martín-Lomas
M
M
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers; D007202:Indicators and Reagents; D008024:Ligands; D009682:Magnetic Resonance Spectroscopy; D008759:Methylglycosides; D008969:Molecular Sequence Data; D015394:Molecular Structure; D012276:Ricin; D013329:Structure-Activity Relationship
D004187:Disaccharides; D004987:Ethers; D007202:Indicators and Reagents; D008024:Ligands; D008759:Methylglycosides; C034207:methyl lactoside; D012276:Ricin