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This work provides an overview of the role of carbohydrates as precursors for the synthesis of heterocycles. It is limited to heterocycles where one or more of their carbon atoms are from carbohydrate reactants. A part of the sugar may remain linked to the heterocycles thus providing nucleoside analogues. The following heterocycles were included: furans, pyrrols, thiophenes, pyrazoles, imidazoles,...
Glycosylamines and glycosyl azides are valuable and versatile intermediates in carbohydrate chemistry; furthermore they are easily available in a highly stereoselective fashion. Glycosylamines and their derivatives glycosyl enamines and glycosyl imines can be transformed into N-glycosyl heterocycles. Glycosyl enamines are also used in the preparation of polyhydroxy pyrrolidines, oxapyrrolizidines,...
The high synthetic versatility exhibited by the isothiocyanato motif has allowed its use as a building block in the preparation of a plethora of derivatives. When present in carbohydrates, the strong electrophilicity shown by isothiocyanates, together with the possibility of undergoing cycloaddition reactions has made it possible to access a broad spectrum of heterocyclic compounds, of either synthetic...
Since more then thirty years carbohydrates have gained much attention as chiral starting materials in stereocontrolled target oriented synthesis. Among variety of applications, synthesis of β-lactam antibiotics from carbohydrate precursors played a special role owing to the importance of these class of compounds in modern chemotherapy. In 1994 we published a review article on the synthesis of β-lactams...
Recent applications of the 1,3-dipolar cycloaddition reaction of azides and alkynes in carbohydrate chemistry are summarized in the present review. The efficient catalyzed version of this reaction, also referred to as one of the so-called click chemistry reactions, has joined in a short period of time a select group of the most efficient and useful organic reactions. In particular, its application...
Porphyrins and carbohydrates are two groups of natural compounds that are vital to our life. However, only a few examples of glycoporphyrins have been isolated from a natural source. The attachment of saccharide units to porphyrin macrocycles gives rise to derivatives which might be of great significance for certain medicinal and other applications. Synthetic methodologies published during the last...
Anisomycin is a natural product that received much attention due to its interesting biological activity against certain pathogenic protozoa, strains of fungi, and in the treatment of certain diseases such as amoebic dysentery and tricomonas vaginitis. This review is focused on the synthesis of natural anisomycin and its analogues. Different approaches to the synthesis of naturally occurring anisomycin...
This review is devoted to the stereoselectivity of intermolecular (intramolecular cycloadditions are not included) 1,3-dipolar cycloadditions of sugar-derived nitrones. Stereoselective cycloaddition (transformation of isoxazolidine followed by reduction of the N–O bond to produce both an amino and a hydroxy function) allows the synthesis of tailor-made products of possible biological interest such...
Anhydro sugars have proved to be versatile chiral synthons for the synthesis of chiral heterocycles including pyradazines, oxazines, triazines, chiral morpholines, tetrahydroquinoxalines, benzodioxins, oxazolidinones, episulfides, thiazolines, and cyclic trithiocarbonates. Selected examples are described in this chapter.
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