144668-22-4Relevant academic research and scientific papers
Synthesis of Carbocyclic Analogues of Guanosine 5'-(β-L-Fucopyranosyl diphosphate) (GDP-Fucose) as Potential Inhibitors of Fucosyltransferases
Cai, Shaopei,Stroud, Mark R.,Hakomori, Senitiroh,Toyokuni, Tatsushi
, p. 6693 - 6696 (1992)
Two carbocyclic analogues of GDP-fucose consisting of 5a-carba-β-L-fucopyranose and its unsaturated counterpart have been synthesized as potential inhibitors of fucosyltransferases through the intramolecular Emmons-Horner-Wadsworth olefination of the 2,6-
Direct synthesis of the isosteric phosphono analogues of α-L-rhamnose 1-phosphate and β-L-fucose 1-phosphate
Cipolla, Laura,La Ferla, Barbara,Panza, Luigi,Nicotra, Francesco
, p. 1003 - 1013 (2007/10/03)
The isosteric phosphono analogue of α-L-rhamnose 1-phosphate has been stereoselectively synthesized by reaction of 2,3,5-tri-O-benzyl-L-rhamnose with tetraethyl methylenediphosphonate and sodium hydride in diglyme, followed by deprotection with iodotrimethylsilane. To synthesize stereoselectively the isosteric phosphono analogue of β-L-fucose 1-phosphate, 2,3,5-tri-O-benzyl-L-fuconolactone was treated with lithiated dimethyl methylenephosphonate, and the 3,4,5-tri-O-benzyl-1,7-dideoxy-1-(phosphonodimethyl)-L-galactoheptulopyranose obtained was stereoselectively reduced with triethylsilane and boron trifluoride etherate to afford the dimethyl (2,3,4-tri-O-benzyl-β-L-fucopyranosyl)methanephosphonate which was finally deprotected with iodotrimethylsilane.
