Synthesis of methyl 2,4-di-O-methyl-3-O-(2-O-methyl-alpha-L-rhamnopyranosyl)-alpha-L- rhamnopyranoside and methyl 2,4-di-O-methyl-3-O-[2-O-methyl-3-O-(2-O-methyl-alpha-L-fucopyranosyl)- alpha-L-rhamnopyranosyl]-alpha-L-rhamnopyranoside: di- and tri-saccharide segments of a phenolic glycolipid of Mycobacterium kansasii.
Syntheses of the title glycosides are described. The critical O-glycosylations were carried out in the presence of boron trifluoride etherate with a high degree of alpha-selectivity.
Gurjar
M K
MK
Indian Institute of Chemical Technology, Hyderabad.
Reddy
K R
KR
D000942:Antigens, Bacterial; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D005643:Fucose / Q000031:analogs & derivatives; D006017:Glycolipids / Q000737:chemistry*; D008969:Molecular Sequence Data; D009161:Mycobacterium / Q000737:chemistry*; D012210:Rhamnose / Q000031:analogs & derivatives; D014312:Trisaccharides / Q000138:chemical synthesis*
D000942:Antigens, Bacterial; D004187:Disaccharides; D006017:Glycolipids; D014312:Trisaccharides; C045169:phenolic glycolipid I, Mycobacterium leprae; C051618:mycoside A; D005643:Fucose; D012210:Rhamnose