Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: In this article, reaction of ribofuranosyl chlorides with 2 eq of 5-lithio-imidazole afforded 1-(5-IMidazolyl)ribofuranoid glycals in good yields.
Abstract: Reaction of ribofuranosyl chlorides with 2 eq of 5-lithio-imidazole afforded 1-(5-imidazolyl)ribofuranoid glycals in good yields. Hydrolysis of the glycal (3) with hydrochloric acid led to 4-(5-hydroxymethylfuran-2-yl)imidazole (7), which contains both hydrophilic and hydrophobic aromatic heterocycles.
TL;DR: In this paper, a methanol-induced kinetic spiroketalization reaction has been developed for the stereocontrolled target and diversity-oriented synthesis of Spiroketals.
Abstract: A methanol-induced kinetic spiroketalization reaction has been developed for the stereocontrolled target- and diversity-oriented synthesis of spiroketals. In contrast to existing methods for spiroketal synthesis, this reaction does not depend on thermodynamic product stability or require axial attack of an oxygen nucleophile. Stereodiverse glycals are alkylated at the C1 position with side chains bearing protected hydroxyl groups. After alcohol deprotection, the glycal is epoxidized stereoselectively, then the side chain hydroxyl is spirocyclized with inversion of configuration at the anomeric carbon by addition of excess MeOH at -63 degrees C. This spirocyclization reaction appears to proceed by MeOH hydrogen-bonding catalysis and has been used to form five- and six-membered rings with stereoisomeric substituents. In some cases, the stereocomplementary spiroketals can be also obtained by classical acid-catalyzed equilibration.
TL;DR: In this paper, N-alkylated tetrahydropyrano[3,2-c ]quinolines were synthesized via intramolecular Friedel-Crafts alkylation using a 1- O -acetylglucosyl derivative as the key intermediate.
Abstract: Diastereoselective synthesis of novel and enantiopure N-alkylated tetrahydropyrano[3,2- c ]quinolines is described via intramolecular Friedel–Crafts alkylation using a 1- O -acetylglucosyl derivative as the key intermediate. Unprecedented formation of new glycal derivatives and α,β-unsaturated carbaldehyde products is also discussed.
Patent•
15 Jun 2018
TL;DR: The xylose carbon glycoside drug is applied to in-vitro cervical cancer resistance and has a significant effect as discussed by the authors, however, it is not suitable for use in the treatment of breast cancer.
Abstract: The invention provides an xylose carbon glycoside drug. A structural formula of the compound is as follows as show in the specification, wherein Ar comprises Ph-, 3-F-Ph- or 3,5-F2-Ph-; and R comprises n-Pr-, PhCH2CH2- or i-Pr-. A preparation method of the drug comprises the steps of preparing full acetylated xylose, xylose bromide and xylose glycal, synthezing an intermediate, namely alkyne ester, taking dichloromethane as a solvent, and adding the alkyne ester intermediate, the xylose glycal and a catalyst for reaction at a room temperature to prepare the xylose carbon glycoside drug. The xylose carbon glycoside drug is applied to in-vitro cervical cancer resistance and has a significant effect.
TL;DR: In this paper, the peracetylated N-acetylneuraminic acid glycal was obtained from the reaction mixture by simple filtration and subsequent evaporation of the solvent.
Abstract: Treatment of the readily available peracetylated N-acetylneuraminic acid glycosyl chloride [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-2,3,5-trideoxy-β-D-glycero-D-galactononulopyranosonate)] with anhydrous Na 2 HPO 4 in refluxing MeCN quantitatively affords the peracetylated N-acetylneuraminic acid glycal [methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2,6-anhydro-D-glycero-D-galacto-non-2-enonate], which can be isolated from the reaction mixture by simple filtration and subsequent evaporation of the solvent. No glycal formation was detected at room temperature even after prolonged treatment with Na 2 HPO 4 . The method proposed is experimentally simple and allows ready preparation of substantial amounts of the title compound, which is an important intermediate in sialic acid chemistry.