ChemInform Abstract: Glycosylidene Carbenes. Part 9. Fullerene Sugars: Preparation of Enantiomerically Pure, Spiro‐Linked C‐Glycosides of C60.

Vasella, A.; Uhlmann, Peter; Waldraff, Christian A. A.; Diederich, François; Thilgen, Carlo

doi:10.1002/chin.199305272

Cited by 2 publications

(2 citation statements)

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“…Spherical topology of the fullerenes has furnished suitable scaffolds for multivalent presentation of peripheral carbohydrate residues, and chemistry has been adapted for their efficient and controlled conjugation. 212 Another approach permitted synthesis of fullerene glycoconjugates via the thermal cycloaddition of the per-O-acetyl glycosyl azides 211 in boiling chlorobenzene. 213 Although this methodology generated a mixture of two inseparable stereoisomers of N-b-glycopyranosyl [5,6]azafulleroids in relatively poor yields (13-28%), the generality of the reaction has been demonstrated with a series of mono-(212, D-glucopyranose and 213, D-galactopyranose), di-(214, lactose and 215, maltose), and trisaccharide (216) conjugates to C 60 .…”

Section: Glycofullerenesmentioning

confidence: 99%

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

309

208

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From the authors' opinion, this chapter constitutes a modest extension of the seminal and inspiring contribution of Stowell and Lee on neoglycoconjugates published in this series [C. P. Stowell and Y. C. Lee, Adv. Carbohydr. Chem. Biochem., 37 (1980) 225-281]. The outstanding progresses achieved since then in the field of the "glycoside cluster effect" has witnessed considerable creativity in the design and synthetic strategies toward a vast array of novel carbohydrate structures and reflects the dynamic activity in the field even since the recent chapter by the Nicotra group in this series [F. Nicotra, L. Cipolla, F. Peri, B. La Ferla, and C. Radaelli, Adv. Carbohydr. Chem. Biochem., 61 (2007) 353-398]. Beyond the more classical neoglycoproteins and glycopolymers (not covered in this work) a wide range of unprecedented and often artistically beautiful multivalent and monodisperse nanostructures, termed glycodendrimers for the first time in 1993, has been created. This chapter briefly surveys the concept of multivalency involved in carbohydrate-protein interactions. The topic is also discussed in regard to recent steps undertaken in glycobiology toward identification of lead candidates using microarrays and modern analytical tools. A systematic description of glycocluster and glycodendrimer synthesis follows, starting from the simplest architectures and ending in the most complex ones. Presentation of multivalent glycostructures of intermediate size and comprising, calix[n]arene, porphyrin, cyclodextrin, peptide, and carbohydrate scaffolds, has also been intercalated to better appreciate the growing synthetic complexity involved. A subsection describing novel all-carbon-based glycoconjugates such as fullerenes and carbon nanotubes is inserted, followed by a promising strategy involving dendrons self-assembling around metal chelates. The chapter then ends with those glycodendrimers that have been prepared using commercially available dendrimers possessing varied functionalities, or systematically synthesized using either divergent or convergent strategies.

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Section: Glycofullerenesmentioning

confidence: 99%

Design and Creativity in Synthesis of Multivalent Neoglycoconjugates

Chabre

Roy

2010

Advances in Carbohydrate Chemistry and Biochemistry

309

208

View full text Add to dashboard Cite

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“…Thermal addition of diazo compounds, followed by thermo or photolysis [74] 2. Addition of free carbenes to C 60 [75] 3. Reactions that proceed by an addition-elimination mechanism [76] 4.…”

Section: Derivatization Reaction Of C 60mentioning

confidence: 99%