Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

New principles for glycoside-bond formation.

Synthetic oligosaccharides and glycoconjugates are increasingly used as probes for biological research and as lead compounds for drug and vaccine discovery. These endeavors are, however, complicated by a lack of general methods for the routine preparation of this important class of compounds. Recent development such as one-pot multi-step protecting group manipulations, the use of unified monosaccharide building blocks, the introduction of stereoselective glycosylation protocols, and convergent strategies for oligosaccharide assembly, are beginning to address these problems. Furthermore, oligosaccharide synthesis can be facilitated by chemo-enzymatic methods, which employ a range of glycosyl transferases to modify a synthetic oligosaccharide precursor. Glycosynthases, which are mutant glycosidases, that can readily form glycosidic linkages are addressing a lack of a wide range glycosyltransferases. The power of carbohydrate chemistry is highlighted by an ability to synthesize glycoproteins.

/pdf/opportunities-and-challenges-in-synthetic-oligosaccharide-4802bp03rp.pdf

Opportunities and challenges in synthetic oligosaccharide and glycoconjugate research

Recent developments in stereoselective 1,2-cis glycosylation that have emerged during the past decade are surveyed herein. For detailed coverage of the previous achievements in the field the reader is referred to our earlier reviews: A. V. Demchenko, Curr. Org. Chem., 2003, 7, 35–79 and Synlett, 2003, 1225–1240.

/pdf/stereocontrolled-1-2-cis-glycosylation-as-the-driving-force-4aabmkgndi.pdf

Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry

Advances in carbohydrate chemistry have certainly made common oligosaccharides much more accessible. However, many current methods still rely heavily upon specialized knowledge of carbohydrate chemistry. The application of automated technologies to chemical and life science applications such as genomics and proteomics represents a vibrant field. These automated technologies also present opportunities for their application to organic synthesis, including that of the synthesis of oligosaccharides. However, application of automated methods to the synthesis of carbohydrates is an underdeveloped area as compared to other classes of biomolecules. The overarching goal of this review article is to present the advances that have been made at the interface of carbohydrate chemistry and automated technology.

/pdf/automated-chemical-oligosaccharide-synthesis-novel-approach-2yzwg5pisi.pdf

Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.

A critical review of the state-of-the-art evidence in support of the mechanisms of glycosylation reactions is provided. Factors affecting the stability of putative oxocarbenium ions as intermediates at the SN1 end of the mechanistic continuum are first surveyed before the evidence, spectroscopic and indirect, for the existence of such species on the time scale of glycosylation reactions is presented. Current models for diastereoselectivity in nucleophilic attack on oxocarbenium ions are then described. Evidence in support of the intermediacy of activated covalent glycosyl donors is reviewed, before the influences of the structure of the nucleophile, of the solvent, of temperature, and of donor–acceptor hydrogen bonding on the mechanism of glycosylation reactions are surveyed. Studies on the kinetics of glycosylation reactions and the use of kinetic isotope effects for the determination of transition-state structure are presented, before computational models are finally surveyed. The review concludes with ...

/pdf/the-experimental-evidence-in-support-of-glycosylation-qm4cq0in86.pdf

The Experimental Evidence in Support of Glycosylation Mechanisms at the SN1–SN2 Interface

Application of 4,5-O,N-oxazolidinone protected thiophenyl sialosyl donor to the synthesis of α-sialosides

Solvent Effect in the Synthesis of Sialosyl α(2–6) Galactosides: Is Acetonitrile the only Choice?

The synthesis of a novel oxazolidinone sialosyl donor is reported. The introduction of a trans-fused ring enhances reactivity and stereoselectivity in glycosylation reactions for the synthesis of α-sialosides. The oxazolidinone ring can also be removed under basic conditions to afford the deprotected amine, which can be further functionalized.

Application of 4,5‐O,N‐Oxazolidinone Protected Thiophenyl Sialosyl Donor to the Synthesis of α‐Sialosides.

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Papers

Application of 4,5-O,N-oxazolidinone protected thiophenyl sialosyl donor to the synthesis of α-sialosides

Solvent Effect in the Synthesis of Sialosyl α(2–6) Galactosides: Is Acetonitrile the only Choice?

Application of 4,5‐O,N‐Oxazolidinone Protected Thiophenyl Sialosyl Donor to the Synthesis of α‐Sialosides.