121570-85-2Relevant articles and documents
Dialkyl imidazolium benzoates - Room temperature ionic liquids useful in the peracetylation and perbenzoylation of simple and sulfated saccharides
Murugesan, Saravanababu,Karst, Nathalie,Islam, Tasneem,Wiencek, John M.,Linhardt, Robert J.
, p. 1283 - 1286 (2003)
Dialkyl imidazolium benzoates, room temperature ionic liquids including 1-ethyl-3-methyl imidazolium benzoate, 1-butyl-3-methyl imidazolium benzoate and 1-hexyl-3-methyl imidazolium benzoate were used in the peracetylation and perbenzoylation of several s
Melophluosides A and B, new triterpene galactosides from the marine sponge Melophlus sarasinorum
Angkouw, Esther D.,Fukumoto, Arina,Hitora, Yuki,Ise, Yuji,Mangindaan, Remy E. P.,Sadahiro, Yusaku,Tsukamoto, Sachiko
, (2020)
Two new triterpene galactosides, melophluosides A and B, were isolated from a marine sponge Melophlus sarasinorum collected in Indonesia. Their structures were determined by the analysis of spectroscopic data and chemical reactions. The absolute configuration of cyclohexenone moiety was determined by the calculated ECD spectrum of a simplified model. Melophluosides A and B exhibited moderate cytotoxicity against HeLa cells (IC50, 11.6 and 9.7 μM, respectively).
Synthesis of a 1,3 β-glucan hexasaccharide designed to target vaccines to the dendritic cell receptor, Dectin-1
Elsaidi, Hassan R.H.,Paszkiewicz, Eugenia,Bundle, David R.
, p. 96 - 106 (2015)
Transformation of 3-O-benzyl-1,2:5,6-di-O-isopropylidene-α-d-glucofuranose into 2,4,6-tri-O-benzoyl-3-O-benzyl glucopyranosyl imidate proceeded efficiently via crystalline benzyl and per-benzoylated derivatives. This imidate glycosylated di-O-isopropylidene-α-d-glucofuranose in high yield and glycosylation of the disaccharide after removal of the 3′-O-benzyl ether afforded the β1,3 linked trisaccharide in excellent yield. Di- and trisaccharides imidates were readily prepared from the furanose terminated glycosylation products but both were unreactive in glycosylation reaction with the debenzylated di- and trisaccharide alcohols. The 3′-O-benzyl perbenzoylated disaccharide pyranose derivative could be selectively debenzoylated and converted to the corresponding perbenzoylated 4,6:4′,6′-di-O-benzylidene derivative. Lewis acid catalyzed glycosidation gave the selectively protected disaccharide ethylthioglycoside in good overall yield. Glycosidation of this thioglycoside donor with 5-methoxycarbonylpentanol gave the disaccharide tether glycoside and after catalytic removal of benzyl ether the resulting disaccharide alcohol was glycosylated by the thioglycoside in a 2+2 reaction to yield a tetrasaccharide. Repetition of selective deprotection of the terminal 3-O-benzyl ether followed by glycosylation by the disaccharide thioglycoside gave a protected hexasaccharide. Hydrogenolysis of this hexasaccharide followed by transesterification and second hydrogenolysis to remove a residual benzyl group gave the target hexasaccharide glycoside 1 as a Dectin-1 ligand functionalized to permit covalent attachment to glycoconjugate vaccines and thereby facilitate improved antigen processing by dendritic cells.
Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. Coli FimH ligands
Mousavifar, Leila,Vergoten, Gérard,Roy, René
, p. 384 - 397 (2018)
C-Allyl –D-mannopyranosides were prepared via a variety of routes to determine an optimal route to the - anomers. The relative conformational energies of the key intermediate was evaluated by molecular modeling which showed the conventional4Cs
Improved anomeric selectivity for the aroylation of sugars
Barros, M. Teresa,Maycock, Christopher D.,Rodrigues, Paula,Thomassigny, Christine
, p. 1373 - 1376 (2004)
By manipulating the solvent and using bulky TMEDA as a base, good yields and improved anomeric selectivities were obtained for the aroylation of D-glucose over similar esterifications using pyridine. The reaction has been extended to mannose and the β-ano
RDC-enhanced NMR spectroscopy in structure elucidation of sucro-neolambertellin
Schuetz, Anne,Murakami, Takanori,Takada, Noboru,Junker, Jochen,Hashimoto, Masaru,Griesinger, Christian
, p. 2032 - 2034 (2008)
(Graph Presented) A new method based on NMR spectroscopy is introduced to determine the absolute configuration of natural compounds and has been successfully applied to sucro-neolambertellin. The method relies on the measurement of residual dipolar coupli
Preparation and activity evaluation of chrysin-β-d-galactopyranoside
Zhu, Zhen-Yuan,Chen, Ling,Liu, Fei,Chen, Li-Jing,Meng, Meng,Sun, Hui-Qing,Zhang, Yong-Min
, p. 1433 - 1440 (2016)
Chrysin-β-d-galactopyranoside was efficiently synthesized, evaluated for its inhibitory activities against H22 cell lines compared with chrysin, the scavenging of hydroxyl radical, DPPH radical and superoxide anion, inhibitory effect against bacteria and
Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides
Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan
supporting information, p. 1874 - 1880 (2019/07/22)
The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.
N-aryl sulfanilamide-N-beta-D-glucopyranose diamide compound and application thereof
-
Paragraph 0029-0030, (2021/06/26)
The invention belongs to the technical field of medicines, and relates to a preparation method and medical application of an N1-aryl sulfanilamide-N4-beta-D-glucopyranose diamide compound. The compound is shown in a general formula (I), substituent groups are described in the specification, and the compound shown in the general formula (I) and an optical active body, a diastereoisomer and a pharmaceutically acceptable salt thereof are applied to preparation of anti-tumor drugs. Based on pharmacophore characteristics and subcellular localization of CA IX and XII, a selective CA IX and XII inhibitor is designed and synthesized, polyhydroxy high-polarity glucose is selected as a tail end, a classical pharmacophore aryl sulfanilamide fragment of a targeted CAs active center is introduced through a flexible aliphatic chain and a rigid aromatic structure, the overall structure can selectively inhibit catalytic activity of extracellular CA IX and XII, an anti-tumor effect is achieved, and therefore, the compound has a good application prospect.
A Substituent-Directed Strategy for the Selective Synthesis of L-Hexoses: An Expeditious Route to L-Idose
See, Nicholas W.,Wimmer, Norbert,Krenske, Elizabeth H.,Ferro, Vito
, p. 1575 - 1584 (2021/03/03)
L-Hexoses are rare but biologically significant components of various important biomolecules. However, most are prohibitively expensive (if commercially available) which limits their study and biotechnological exploitation. New, efficient methods to access L-hexoses and their derivatives are thus of great interest. In a previous study, we showcased a stereoselective Bu3SnH-mediated transformation of a 5-C-bromo-D-glucuronide to an L-iduronide. We have now drawn inspiration from this result to derive a new methodology – one that can be harnessed to access other L-hexoses. DFT calculations demonstrate that a combination of a β-F at the anomeric position and a methoxycarbonyl substituent at C-6 is key to optimising the selectivity for the L-hexose product. Our investigations have also culminated in the development of the shortest known synthetic route to a derivative of L-idose from a commercially available starting material (45 % yield over 3 steps). Collectively, these results address the profound lack of understanding of how to synthesise L-hexoses in a stereoselective fashion.
