Synthesis of 4” manipulated Lewis X trisaccharide analogues

• Christopher J. Moore and
• France-Isabelle Auzanneau

Beilstein J. Org. Chem. 2012, 8, 1134–1143, doi:10.3762/bjoc.8.126

• yields. Keywords: chlorodeoxygalactose; fluorodeoxygalactose; Lewis X analogues; oligosaccharide synthesis; Introduction A glycolipid displaying the dimeric Lex hexasaccharide (dimLex) has been identified as a cancer associated carbohydrate antigen, particularly prevalent in colonic and liver

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

• Hemali D. Premathilake and
• Alexei V. Demchenko

Beilstein J. Org. Chem. 2012, 8, 597–605, doi:10.3762/bjoc.8.66

• oligosaccharide synthesis [6]. However, suitable reaction conditions for the orthogonal activation of these two classes of leaving groups are yet to be found. Commonly, O-glycosides are too stable to be used as effective glycosyl donors [21]. Pent-4-enyl O-glycosides introduced by Fraser-Reid are unique in this

• a more flexible approach for oligosaccharide synthesis. Concomitantly with our studies, Hung et al. came up with essentially the same idea and reported the synthesis of AP mannosides and their activation for O-mannosylation in the presence of ICl/AgOTf [27]. The following considerations driving our

• building blocks in oligosaccharide synthesis. Glycosylation of AP glycosyl donors 1a–d. AP glycosides as glycosyl donors and acceptors in chemoselective and selective activations. Supporting Information Supporting Information File 156: Experimental procedures, extended experimental data, 1H and 13C NMR

Electrochemical generation of 2,3-oxazolidinone glycosyl triflates as an intermediate for stereoselective glycosylation

• Toshiki Nokami,
• Akito Shibuya,
• Yoshihiro Saigusa,
• Shino Manabe,
• Yukishige Ito and
• Jun-ichi Yoshida

Beilstein J. Org. Chem. 2012, 8, 456–460, doi:10.3762/bjoc.8.52

• Stereoselective formation of glycosidic linkages is the key issue in oligosaccharide synthesis, because both 1,2-trans and 1,2-cis aminoglycosides are ubiquitous in biologically active oligosaccharides [1][2][3][4][5]. The 1,2-trans aminoglycosides, which are found in Nod factor [1] and lipid A [2], can be easily

Synthesis in the glycosciences II

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2012, 8, 411–412, doi:10.3762/bjoc.8.45

• . Expertise and rational planning have allowed the utilization of carbohydrates in stereoselective synthesis and the employment of enzymes in oligosaccharide synthesis. Analytical and pharmacological knowhow have disclosed polysaccharide and glycoconjugate structures, their biological effects and their

Synthesis of 6-PEtN-α-D-GalpNAc-(1–>6)-β-D-Galp-(1–>4)-β-D-GlcpNAc-(1–>3)-β-D-Galp-(1–>4)-β-D-Glcp, a Haemophilus influenzae lipopolysacharide structure, and biotin and protein conjugates thereof

• Andreas Sundgren,
• Martina Lahmann and
• Stefan Oscarson

Beilstein J. Org. Chem. 2010, 6, 704–708, doi:10.3762/bjoc.6.80

• the title compound have been constructed to allow further use in biological experiments. Keywords: conjugate vaccines; glycoconjugates; Haemophilus influenzae; lacto-N-neotetraose; oligosaccharide synthesis; thioglycosides; Introduction Haemophilus influenzae are Gram-negative bacteria divided into

Synthesis in the glycosciences

• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2010, 6, No. 16, doi:10.3762/bjoc.6.16

• . Since the isolation of those complex glycans which are active in cellular communication is problematic, oligosaccharide synthesis is an important area of research. Moreover, what Professor Hans Paulsen, one of the greatest exponents of glycoside synthesis, observed in 1982 [2] still holds true today

• : “Although we have now learned to synthesize oligosaccharides, it should be emphasized that each oligosaccharide synthesis remains an independent problem, whose resolution requires considerable systematic research and a good deal of know-how. There are no universal reaction conditions for oligosaccharide

• syntheses”. It is therefore not surprising that the majority of contributions collected in this Thematic Series deal with methods, both chemical and enzymatic, for oligosaccharide synthesis. One approach to deal with the problem of glycoside synthesis is the preparation of so-called glycomimetics. This is a

Acid- mediated reactions under microfluidic conditions: A new strategy for practical synthesis of biofunctional natural products

• Katsunori Tanaka and
• Koichi Fukase

Beilstein J. Org. Chem. 2009, 5, No. 40, doi:10.3762/bjoc.5.40

• the βMan(1→4)GlcNTroc fragment c of N-linked glycans, is another challenging topic in oligosaccharide synthesis. Various methods, such as intramolecular aglycon delivery (IAD) or glycosylation with 4,6-O-benzylideneacetal-protected α-mannosyltriflates, have recently been reported and successfully