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Volumn , Issue 10, 2011, Pages 1803-1825

Metathesis reactions of carbohydrates: Recent highlights in alkyne metathesis

Author keywords

Alkenes; Alkynes; Carbohydrates; Glycoconjugates; Metathesis

Indexed keywords


EID: 79952945950     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.201001518     Document Type: Review
Times cited : (30)

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    • Also in this report, a new, highly potent activator for molybdenum hexacarbonyl and 2-fluorophenol is described. The "instant" catalyst formed in situ from hexacarbonylmolybdenum and 2-fluorophenol shows high activity in the cross- and ring-closing alkyne metathesis reaction. On the other hand, polymerization of phenylacetylene by Lewis-acid-activated tungsten carbonyl complexes is a well-known reaction. See, for instance
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    • trans-Fused polycyclic ethers are widely distributed in nature. For instance, the first example of a marine toxin featuring a trans-fused polycyclic ethers motif, brevetoxin B, was isolated and fully characterized in 1981. Since then, these molecules have attracted attention due to their biological activity, scarcity from natural sources, and complex molecular architecture. For some selected reviews covering the occurrence, biological activity, and synthetic approaches to these types of compounds, see
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    • In general C-vinyl glycosides are poor metathetical partners although different reasons have been advanced to justify this behavior. For selected references, see
    • In general C-vinyl glycosides are poor metathetical partners although different reasons have been advanced to justify this behavior. For selected references, see
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    • Two-directional CM reactions are also a very useful tool in organic synthesis. For some selected recent accounts, see
    • Two-directional CM reactions are also a very useful tool in organic synthesis. For some selected recent accounts, see
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    • The formation of dimeric products in RCEYM reactions has been reported. See, for instance
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    • [62] the authors pointed out that "molecular models of compound 101b showed severe transannular interactions due to the bulky β-OTES group". In our opinion these stereochemical differences might also play an important role regarding the appropriate orientation of the reactive fragments in intermediate 91 (Scheme 20) in connection with the final RCM reaction
    • [62] the authors pointed out that "molecular models of compound 101b showed severe transannular interactions due to the bulky β-OTES group". In our opinion these stereochemical differences might also play an important role regarding the appropriate orientation of the reactive fragments in intermediate 91 (Scheme 20) in connection with the final RCM reaction.
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    • Vinylcyclohexene and, to a lesser extent, vinylcyclopentene derivatives are useful synthetic building blocks because of their Diels-Alder cycloadditions. For selected references, see
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    • For selected recent examples of the synthesis and biological activity of spiro-C-glycosides, see
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    • In different studies on the Diels-Alder cycloaddition of carbohydrate-derived dienes and their carbocyclic (vinylcyclohexene) analogues bearing a methoxy group at the allylic position, it was observed that the reaction occurs with a preference for addition of the dienophile (N-phenylmaleimide, dimethyl acetylenedicarboxylate, diethyl azodicarboxylate, and N-phenyl-1,2,4-triazoline-3,5-dione) to the face of the diene opposite to the allylic methoxy group, see
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    • "Natural product hybrids" are composed of substructures originating either from different biosynthetic pathways or containing several biological functions. These fragments are hybridized by Nature to generate naturally occurring conjugates. Such hybrids include the well-known glycosylated steroids, glycosylated or lipidated peptides, or polyketide alkaloids. For some selected reviews, see
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    • Different alkynes were tested and only experiments with yields over 60 % are indicated in Scheme 34.
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    • The conformations shown below are favored for both the cis and trans isomers of compounds 204 due to the anomeric effect. The trans isomer is more stable because of the pseudo-equatorial position of the carboxyethyl group
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    • Photodynamic therapy (PDT) is an anticancer treatment for solid tumors among other diseases. In these cases the drug is a photosensitizer that is selectively retained in the tumor. When these photosensitizers are exposed to a specific wavelength, they are excited to an excited singlet state which undergoes intersystem crossing to a longer-lived excited triplet state. In this excited state the photosensitizer is able to react with oxygen to produce an excited single-state oxygen molecule, which reacts with the appropriate biomolecule through destructive reactions producing apoptosis or necrosis of the tumoral cells. Among typical photosensitizing agents for PDT are porphyrin derivatives, phthalocyanins, chlorin derivatives, colorants (such as methylene blue), anthraquinone derivatives (such as hypericin), and 5-aminolevulinic acid (a biogenetic precursor of porphyrins). For some selected reviews on PDT, see
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    • Galectins are a family of carbohydrate-binding proteins with an affinity for β-galactosides. These compounds have been strongly implicated in inflammation and cancer, and may be useful targets in the development of new anti-inflammatory and anti-cancer therapies. Twelve members of this family have been reported for humans so far and, although all galectins bind lactose and other β-galactosides, they differ in their affinity for more complex saccharides. The relationship between galectins and cancer is well documented. Most of the evidence is correlatory, that is, more galectin in more malignant tumors, but the direct evidence comes from mouse models. For instance, in paired tumor cell lines (with decreased or increased expression of galectin-3) the one with more galectin-3 gives more tumors and metastasis. As a consequence, carbohydrates, or modified carbohydrates that inhibit galectin-3 could inhibit tumors in vivo. For selected reviews, see
    • Galectins are a family of carbohydrate-binding proteins with an affinity for β-galactosides. These compounds have been strongly implicated in inflammation and cancer, and may be useful targets in the development of new anti-inflammatory and anti-cancer therapies. Twelve members of this family have been reported for humans so far and, although all galectins bind lactose and other β-galactosides, they differ in their affinity for more complex saccharides. The relationship between galectins and cancer is well documented. Most of the evidence is correlatory, that is, more galectin in more malignant tumors, but the direct evidence comes from mouse models. For instance, in paired tumor cell lines (with decreased or increased expression of galectin-3) the one with more galectin-3 gives more tumors and metastasis. As a consequence, carbohydrates, or modified carbohydrates that inhibit galectin-3 could inhibit tumors in vivo. For selected reviews, see
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.