28708-32-9Relevant academic research and scientific papers
First Analog of Pyrimidine Nucleosides with Two D-Ribofuranose Residues
Belenok, M. G.,Kataev, V. E.,Saifina, L. F.,Semenov, V. E.,Sharipova, R. R.
, p. 181 - 184 (2020)
The reaction of 1,3-bis(pent-4-yn-1-yl)-6-methyluracil with 2,3,5-tri-O-acetyl-β-D-ribofuranosyl azide gave 1,3-bis{3-[1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl}-6-methyluracil which was deprotected by treatment with a solution of sodium methoxide in methanol to obtain 1,3-bis{3-[1-(β-D-ribofuranosyl)-1H-1,2,3-triazol-4-yl]propyl]-6-methyluracil as a first analog of pyrimidine nucleosides containing two D-ribofuranose fragments.
A Synthesis Strategy for the Production of a Macrolactone of Gulmirecin A via a Ni(0)-Mediated Reductive Cyclization Reaction
Ichikawa, Satoshi,Katsuyama, Akira,Kitahata, Shun
supporting information, (2020/03/30)
A synthesis strategy for the production of a key synthetic intermediate of gulmirecin A was described. The key reaction in the preparation of the 12-membered macrolactone is the Ni(0)-mediated reductive cyclization reaction of ynal using an N-heterocyclic carbene ligand and silane reductant. In addition, the α-selective glycosylation reaction of the macrolactone was performed to demonstrate the synthesis of gulmirecin and disciformycin precursors.
Mild Palladium-Catalyzed Cyanation of Unprotected 2-Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2-Glycoanalogues
Ferry, Angélique,Lubin-Germain, Nadège,Malinowski, Maciej,Van Tran, Thanh,de Robichon, Morgane
supporting information, (2020/02/11)
Access to unprotected 2-cyano-glycals via a mild palladium-catalyzed cyanation of protecting groups-free 2-iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide-type were successfully obtained in good to excellent yields. These unprotected 2-cyano-glycal scaffolds were successfully derivatized to different C2-glycoanalogues. (Figure presented.).
Design, synthesis and biological evaluation of carbohydrate-based sulphonamide derivatives as topical antiglaucoma agents through selective inhibition of carbonic anhydrase II
Fan, Zhanfang,Guo, Chun,Hou, Zhuang,Li, Chuanchao,Lin, Bin,Liu, Yang,Liu, Yichuang,Wang, Yitong,Zhang, Miao
, p. 383 - 390 (2019/12/30)
A series of new carbohydrate-based sulphonamide derivatives were designed, synthesised by employing the so-call ‘sugar-tail’ approach. The compounds were evaluated in vitro against a panel of CAs. Compared to their parent compound p-sulfamoylbenzoic acid, these compounds showed nearly 100-fold improvement in their binding affinities against hCA II in vitro. All of compounds showed great water solubility and the pH value of their water solutions of compounds is 7.0. Such properties are advantageous to make them much less irritating to the eye when applied topical glaucomatous drugs, compared to the relatively highly acidic dorzolamide preparations (pH 5.5). Notably, compounds 7d, 7 g, 7 h demonstrated to topically lower intraocular pressure (IOP) in glaucomatous animals better than brinzolamide when applied as a 1% solution directly into the eye. Low cytotoxicity on human cornea epithelial cell was observed in the tested concentrations by the MTT assay.
Palladium catalyzed stereocontrolled synthesis of C-aryl glycosides using glycals and arenediazonium salts at room temperature
Singh, Adesh Kumar,Kandasamy, Jeyakumar
supporting information, p. 5107 - 5112 (2018/07/29)
A stereocontrolled synthesis of aryl-C-glycosides was achieved using glycals and aryldiazonium salts in the presence of palladium acetate. A wide range of glycals including d-glucal, d-galactal, l-rhamnal, d-xylal and d-ribal underwent C-arylation at the anomeric carbon in the presence of different aryldiazonium tetrafluoroborates and gave synthetically useful 2,3-deoxy-3-keto-α-aryl-C-glycosides in good to excellent yields. Broad substrate scope, simple operation and room temperature reactions make this protocol very attractive in organic synthesis.
Stereoselective acetylation of hemicellulosic C5-sugars
Herde, Zachary D.,John, Prathap D.,Alvarez-Fonseca, Dania,Satyavolu, Jagannadh,Burns, Christopher T.
, p. 1 - 14 (2017/03/21)
The stereoselective peracetylation of α-D-xylose (1) and α-L-arabinose (4) using a combination of triethylamine and acetic anhydride in the presence or absence of a catalytic amount of dimethylaminopyridine (DMAP) is described. The peracetylated D-xylose and L-arabinose alpha pyranose anomers 2α and 5α are obtained in 97% and 56% yields respectively. The peracetylated D-xylose beta pyranose anomer 2β is obtained in 71% yield through simple modification of the reaction conditions. Details regarding synthesis and isolation optimization studies under different conditions are presented below. The stereoselective peracetylation reactions disclosed here have been used to separate mixtures of D-xylose and L-arabinose as their peracetylated derivatives 2β and 5α in 47% and 42% yields and can provide pure pentoses after deacetylation.
Molecular sieves mediated green per-O-acetylation of carbohydrate templates and lipase catalyzed regioselective alcoholysis of 2,3,5-Tri-O-acetyl-D-ribonolactone
Cardozo, Herbert M.,Ribeiro, Thaís F.,Sá, Marcus M.,Sebr?o, Damianni,Nascimento, Maria G.,Silveira, Gustavo P.
, p. 755 - 764 (2015/04/14)
The per-O-acetylation of D-ribono-1,4-lactone and representative carbohydrates through the combination of acetic anhydride and molecular sieves under solvent-free conditions is demonstrated. The use of 13X/KCl molecular sieves as the heterogeneous catalyst was found to be more efficient than the excess of pyridine normally employed in the conventional method, giving high yields of the expected peracetylated product after 3 h at 25 °C or 1 h at 50 °C. The transformation can be carried out in gram scale and in an open flask. Additionally, the catalyst is readily separated from the reaction medium and can be reutilized without significant loss of activity. This green procedure for acetylation was extended to D-ribonolactone derivatives and natural carbohydrates. To demonstrate the synthetic utility of the method, 2,3,5-tri-O-acetyl-D-ribonolactone was selected as the substrate for the regioselective alcoholysis of acetyl group catalyzed by Candida antarctica lipase B in EtOH to selectively produce 2,3-di-O-acetyl-D-ribonolactone in gram scale.
Effect of acyl chain length on selective biocatalytic deacylation on O-aryl glycosides and separation of anomers
Aggarwal, Neha,Arya, Anu,Mathur, Divya,Singh, Sukhdev,Tyagi, Abhilash,Kumar, Rajesh,Rana, Neha,Singh, Rajendra,Prasad, Ashok K.
, p. 83 - 91 (2014/04/03)
It has been demonstrated that Lipozyme TL IM (Thermomyces lanuginosus lipase immobilised on silica) can selectively deacylate the ester function involving the C-5′ hydroxyl group of α-anomers over the other acyl functions of anomeric mixture of peracylate
Solvent-free per-O-acetylation of carbohydrates
Cai, Li,Rufty, Chris,Liquois, Megan
, p. 4367 - 4369 (2014/08/05)
A facile, solvent-free acetylation method promoted by commercial 4? molecular sieves is described here for the synthesis of per-Oacetylated carbohydrates, which are important intermediates in carbohydrate chemistry. Several examples of carbohydrate and noncarbohydrate substrates are provided.
Two-step synthesis of per-O-acetylfuranoses: Optimization and rationalization
Dureau, Remy,Legentil, Laurent,Daniellou, Richard,Ferrieres, Vincent
experimental part, p. 1301 - 1307 (2012/04/04)
A simple two-step procedure yielding peracetylated furanoses directly from free aldoses was implemented. Key steps of the method are (i) highly selective formation of per-O-(tert-butyldimethylsilyl)furanoses and (ii) their clean conversion into acetyl ones without isomerization. This approach was easily applied to galactose and structurally related carbohydrates such as arabinose, fucose, methyl galacturonate and N-acetylgalactosamine to give the corresponding peracetylated targets. The success of this procedure relied on the control of at least three parameters: (i) the tautomeric equilibrium of the starting unprotected oses, (ii) the steric hindrance of both targeted furanoses and silylating agent, and finally, (iii) the reactivity of each soft nucleophile during the protecting group interconversion.
