408534-93-0Relevant academic research and scientific papers
Synthesis of the C-disaccharide α-C(1→3)-L-fucopyranoside of N-acetylgalactosamine
Viode, Cecile,Vogel, Pierre
, p. 733 - 746 (2001)
Radical C-glycosidation of racemic 5-exo-benzeneselenyl-6-endo-chloro-3-methylidene-7-oxabicyclo[2.2.1]heptan-2-one ((±)-2) with α-acetobromofucose (3) provided a mixture of α-C-fucosides that were reduced with NaBH4 to give two diastereomeric alcohols that were separated readily. One of them ((-)-6) was converted into (-)-methyl 2-acetamido-4-O-acetyl-2,3-dideoxy-3-C-(3′,4′,5′-tri-O-acetyl- 2′,6′-anhydro-1′ ,7′-dideoxy-α-L-glycero-D-galacto-heptitol-1′ -C-yl)-α -D-galactopyranuronate ((-)-11) and then into (-)-methyl 2-acetamido-2,3-dideoxy-3-C-(2′,6′-anhydro-1′,7′-dideoxy -a-L-glycero-D-galacto-heptitol-1′ -C-yl)-β -D-galactopyranoside ((-)-1), a new α-C(1→3)-L-fucopyranoside of N-acetylgalactosamine. Its 1H NMR data shows that this C-disaccharide (α-L-Fucp-(1→3)CH2-β-D-Ga1NAc-OMe) adopts a major conformation in solution similar to that expected for the corresponding O-linked disaccharide, i.e., with antiperiplanar σ(C-3′,C-2′) and σ(C-1′,C-3) bonds.
