Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide.
Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a d-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.
McCartney
Jason L
JL
Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, Ohio 44555-3663, USA.
Meta
Christopher T
CT
Cicchillo
Robert M
RM
Bernardina
Matthew D
MD
Wagner
Timothy R
TR
Norris
Peter
P
D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D007783:Lactones / Q000737:chemistry*; D008094:Lithium / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry; D011807:Quinolizines / Q000737:chemistry; D012266:Ribose / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry; D014961:X-Ray Diffraction
D004187:Disaccharides; D006027:Glycosides; D007783:Lactones; D009942:Organometallic Compounds; D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; D012266:Ribose; D008094:Lithium