Preparation, characterization, and biological evaluation of 6I,6IV-di-O-[α-l-fucopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]-cyclomaltoheptaose and 6-O-[α-l-fucopyranosyl-(1→6)-2-acetamido-2-deoxy-β-d-glucopyranosyl]-cyclomaltoheptaose

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2011–2012

“…CuI-catalyzed azidealkyne cycloaddition from mono-6-azido--cyclodextrin Cyclomaltoheptaose derivs TOF (DHB) With -Fuc-GlcNAc and -Fuc--GlcNAc substituents (Nakagawa et al, 2011d) 6-Deoxyacrylamido--and --cyclodextrins TOF Discriminate between 1-naphthyl-and 2-naphthyl-methyl moieties (Zheng et al, 2011b) 6-Deoxy-6-amino--cyclodextrin TOF…”

Development of Fully and Partially Protected Fucosyl Donors for Oligosaccharide Synthesis

“…It was concluded that the problems observed with the two-stage glycosylation must occur after the bromination step. A number of literature examples of α-Fuc-(1–6)-GlcNAc synthesis highlight the extremely labile nature of the biologically important α-(1–6) linkage. , Kunz et al showed that the presence of arming groups such as benzyl protection on the fucose increase the instability of the α-(1–6) glycosidic bond . The highly reactive nature of the donor 7 , coupled with the sensitive glycosidic bond in the product 9 , was identified as the main reason for the low yields in the glycosylation reactions screened.…”

Direct and Regioselective Di‐α‐fucosylation on the Secondary Rim of β‐Cyclodextrin

“…[9] Most examples of chemically synthesized glycoclusters display the glycanso nt he primary rim, [10][11][12][13][14][15][16][17] and only af ew examples are reported of direct glycosylation of the C6 hydroxyls. [18][19][20][21] Alternatively,e nzymatic transglycosylation strategies resulted in the formation of am ixture of multiply glycosylated CDs, bearing a-galactosyl units on the C-2 or C-6 positiono ft he glucosides. [22,23] When two or more glycoside units were introduced, low regioselectivityw as observed.…”

“…As depicted in Scheme , CDs generally adopt the shape of a truncated cone, which has the C‐6 hydroxyls on the top (primary rim) and the C‐2 and C‐3 hydroxyls on the bottom of the cone (secondary rim, Scheme ) . Most examples of chemically synthesized glycoclusters display the glycans on the primary rim, and only a few examples are reported of direct glycosylation of the C6 hydroxyls . Alternatively, enzymatic transglycosylation strategies resulted in the formation of a mixture of multiply glycosylated CDs, bearing α‐galactosyl units on the C‐2 or C‐6 position of the glucosides .…”