- Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System
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For the first time, an inclusion complex has been crafted between a carbohydrate-based molecule and a β-cyclodextrin (CD) hydrophobic cavity for asymmetric catalytic applications. This novel d-glucosamine-based inclusion compound has been synthesized in h
- Rani, Dhiraj,Sethi, Aaftaab,Kaur, Khushwinder,Agarwal, Jyoti
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p. 9548 - 9557
(2020/09/09)
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- New phosphine-imine and phosphine-amine ligands derived from D-gluco-, D-galacto- and D-allosamine in Pd-catalysed asymmetric allylic alkylation
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New phosphine-imine and phosphine-amine chiral ligands which were easily prepared from D-gluco-, D-galacto- and D-allosamine furnished a high level of enantiomeric excess (up to 99%) in the Pd(0)-catalysed asymmetric allylic alkylation of racemic 1,3-diphenyl-2-propenyl acetate with malonates.
- Szulc, Izabela,Ko?odziuk, Robert,Zawisza, Anna
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p. 1476 - 1485
(2018/02/19)
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- Ring-Opening Reactions of the N-4-Nosyl Hough-Richardson Aziridine with Nitrogen Nucleophiles
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Dinosylated α-d-glucopyranoside was directly transformed into α-d-altropyranosides via in situ formed N-4-nosyl Hough-Richardson aziridine with nitrogen nucleophiles under mild conditions in fair to excellent yields. The scope of the aziridine ring-opening reaction was substantially broadened contrary to the conventional methods introducing solely the azide anion at high temperatures. If necessary, the N-4-nosyl Hough-Richardson aziridine can be isolated by filtration in a very good yield and high purity.
- Ru?il, Tomá?,Trávní?ek, Zdeněk,Canka?, Petr
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p. 723 - 730
(2017/04/26)
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- Sugar derived alkamine catalytic imine reduction method
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The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.
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Paragraph 0040; 0041; 0042
(2016/10/07)
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- D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides
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D-Glucosamine was successfully employed as a chiral auxiliary for the enantioselective synthesis of phosphine oxides. The influence of the anomeric position was also investigated and revealed the excellent ability of the α-anomer to perform this transform
- D'Onofrio,Copey,Jean-Gérard,Goux-Henry,Pilet,Andrioletti,Framery
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supporting information
p. 9029 - 9034
(2015/09/01)
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- Diaminohexopyranosides as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes
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The syntheses of methyl 2,3-diamino-4,6-O-benzylidene-2,3-dideoxy-α-d-hexopyranosides of glucose, mannose, gulose, and talose and methyl 2-amino-4,6-benzylidene-2,3-dideoxy-3-tosylamido-α-d-glucopyranoside are exhaustively presented, as well as their application as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes. The complex formation occurs highly diastereoselectively, creating a stereogenic metal center. The molecular structures of the ligands and their complexes were investigated by X-ray structure analysis, NMR spectroscopy, polarimetry, and DFT methods. The diamino monosaccharide complexes have been subjected to antitumor activity studies. In vitro tests of a few ruthenium complexes against different cancer cell types showed antiproliferative activities 4-10 times lower than that of cisplatin.
- B?ge, Matthias,Fowelin, Christian,Bednarski, Patrick,Heck, Jürgen
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supporting information
p. 1507 - 1521
(2015/05/13)
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- 3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes
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The 4-ulose and the 3-ulose, both derived in two steps from the α-methyl glycoside of N-acetyl-D-glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with α,β-unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively. Copyright
- Schoeberl, Christof,Jaeger, Volker
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supporting information; experimental part
p. 790 - 796
(2012/05/04)
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- 2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one-pot sequential functionalisation of glycosides for the generation of orthogonally protected monosaccharide building blocks
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Orthogonally protected monosaccharide building blocks have been prepared using TCT in a one-pot multicomponent transformation. The process involves successive steps of arylidene acetalation, esterification and regioselective reductive acetal cleavage. High regioselectivity, scope for using a broad range of substrates, functional group tolerance, mild reaction conditions, easy handling process and wide application range are a few advantages of the current process.
- Tatina, Madhubabu,Yousuf, Syed Khalid,Mukherjee, Debaraj
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supporting information; experimental part
p. 5357 - 5360
(2012/07/30)
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- Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction
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Glucosamine derivatives have been synthesized starting from commercially available N-acetyl-D-glucosamine/glucosamine hydrochloride and have been employed successfully as efficient organocatalysts for the direct asymmetric aldol reaction between cyclohexa
- Agarwal, Jyoti,Peddinti, Rama Krishna
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scheme or table
p. 3502 - 3505
(2011/06/21)
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- Synthesis and characterization of d-glucosamine-derived low molecular weight gelators
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Carbohydrate-based low molecular weight gelators are an interesting class of molecules with many potential applications. Previously, we have found that certain esters and carbamates of 4,6-O-benzylidene-α-d-methyl- glucopyranoside are low molecular weight
- Goyal, Navneet,Cheuk, Sherwin,Wang, Guijun
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supporting information; experimental part
p. 5962 - 5971
(2010/09/18)
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- Accessible sugars as asymmetric olefin epoxidation organocatalysts: Glucosaminide ketones in the synthesis of terminal epoxides
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A systematically varied series of conformationally restricted ketones, readily prepared from N-acetyl-d-glucosamine, were tested against representative olefins as asymmetric epoxidation catalysts showing useful selectivities against terminal olefins and, in particular, typically difficult 2,2-disubstituted terminal olefins.
- Boutureira, Omar,McGouran, Joanna F.,Stafford, Robert L.,Emmerson, Daniel P. G.,Davis, Benjamin G.
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supporting information; experimental part
p. 4285 - 4288
(2009/12/05)
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- A 1-acetamido derivative of 6-epi-valienamine: An inhibitor of a diverse group of β-N-acetylglucosaminidases
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The synthesis of an analogue of 6-epi-valienamine bearing an acetamido group and its characterisation as an inhibitor of β-N- acetylglucosaminidases are described. The compound is a good inhibitor of both human O-GlcNAcase and human β-hexosaminidase, as well as two bacterial β-N-acetylglucosaminidases. A 3-D structure of the complex of Bacteroides thetaiotaomicron BtGH84 with the inhibitor shows the unsaturated ring is surprisingly distorted away from its favoured solution phase conformation and reveals potential for improved inhibitor potency. This journal is The Royal Society of Chemistry.
- Scaffidi, Adrian,Stubbs, Keith A.,Dennis, Rebecca J.,Taylor, Edward J.,Davies, Gideon J.,Vocadlo, David J.,Stick, Robert V.
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p. 3013 - 3019
(2008/04/01)
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- Carbohydrate-derived aminoalcohol ligands for asymmetric Reformatsky reactions
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Members of a family of functionally and stereochemically diverse d-glucosamine-derived tertiary aminoalcohol ligands have been used to promote the asymmetric Reformatsky reaction. The β-hydroxyester product tert-butyl 3-phenyl-3-hydroxy-propanoate was obt
- Emmerson, Daniel P.G.,Hems, William P.,Davis, Benjamin G.
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p. 213 - 221
(2007/10/03)
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- Synthesis of two oligosaccharides, the GPI anchor glycans from S. cerevesiae and A. fumigatus
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Two oligosaccharides, α-D-Manp-(1→2)-α-D-Manp-(1→2)- α-D-Manp-(1→6)-α-D-Manp-(1→4)-α-D-GlcpNAc (I) and α-D-Manp-(1→3)-α-D-Manp-(1→2)-α-D-Manp-(1→2) -α-D-Manp-(1→6)-α-D-Manp-(1→4)-α-D-GlcpNAc (II), the glycosylphosphatidylinositol (GPI) anchor glycans from
- Ma, Zuchao,Zhang, Jianjun,Kong, Fanzuo
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- Precise structure activity relationships in asymmetric catalysis using carbohydrate scaffolds to allow ready fine tuning: dialkylzinc-aldehyde additions.
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The ready construction of 24 stereochemically and functionally diverse carbohydrate ligand structures from a core D-glucosamine scaffold has allowed the evaluation of broad ranging structure activity relationships in ligand accelerated zincate additions t
- Emmerson, Daniel P G,Villard, Renaud,Mugnaini, Claudia,Batsanov, Andrei,Howard, Judith A K,Hems, William P,Tooze, Robert P,Davis, Benjamin G
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p. 3826 - 3838
(2007/10/03)
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- Stereoselective Preparation of Deuterium-Labeled Sugars: (6R)-(6-2H1)-N-Acetylglucosamine Derivatives
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The preparation of methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-α-D-glucose (8α-d) and methyl (6R)-(6-2H1)-2-deoxy-2-N-acetamido-β-D-glucose (8β-d) is described. The key step in the synthesis was the stereoselective reduction of a C6-aldehydo-GlcNAc derivative with (R)-(+)-Alpine-Borane-d. Reduction of either methyl 6-aldehydo-3,4-di-O-benzyl-α-GlcNAc (6α) or methyl 6-aldehydo-3,4-di-O-benzyl-β-GlcNAc (6β) using (R)-(+)-Alpine-Borane-d in CH2Cl2 was significantly more stereoselective (>15:1 stereoselectivity for both anomers) than was reduction with NaBD4 in MeOH. The absolute stereochemistry at C6 of the deuterated GlcNAc derivatives was determined from 1H NMR analysis of the conformationally locked sugars, methyl (6R)-(6-2H 1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-α-D-glucose (9α-d) and methyl (6R)-(6-2H 1)-4,6-O-benzylidene-2-deoxy-2-N-acetamido-β-D-glucose (9β-d). Comparison of 3JH5,H6 values and 1H-1H NOEs for the nondeuterated and deuterated benzylidene derivatives showed that reduction with (R)-(+)-Alpine-Borane-d gave the (6R)-(G-2H1) epimer as the major product for both the GlcNAc α and β methyl glycosides. This stereoselective reduction enabled the 1H NMR signals for the prochiral H6 and H6′ protons in a series of GlcNAc derivatives to be assigned.
- Falcone-Hindley, Margaret L.,Davis, Jeffery T.
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p. 5555 - 5561
(2007/10/03)
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- Synthesis of 1D-(1,3,5/2,4)-4-acetamido-5-amino-1,2,3-cyclohexanetriol and its incorporation into a pseudo-disaccharide
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The synthesis of the title compound and 1D-(1,3,5/2,4)-4-acetamido-5-amino-3-O-(β-D-glucopyranosyluronic acid)-1,2,3-cyclohexanetriol is described.Starting from methyl 2-acetamido-2-deoxy-α-D-glucopyranoside 2L-(2,4,5/3)-4-acetamido-3-benzoyloxy-2-benzylo
- Wang, Lai-Xi,Sakairi, Nobuo,Kuzuhara, Hiroyoshi
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- Further Aspects of the Reduction of Dithiocarbonates with Tributyltin Hydride and Deuteride
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The reduction of 1,2:5,6-di-O-isopropylidene-3-O-(methylthio)thiocarbonyl-β-D-idose, -talose, and -(3-(2H))talose with tributyltin hydride and deuteride leads to the deoxy sugar and some deuteriumcontaining deoxy sugars.A modification of the normal procedure allows for reduction with tributyltin hydride generated in situ.As well, the reduction of some dithiocarbonates derived from glycosides of N-acetyl-D-glucosamine allows to a variety of dideoxy and trideoxy sugars.
- Conway, Richard J.,Nagel, Jennifer P.,Stick, Robert V.,Tilbrook, D. Matthew G.
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p. 939 - 945
(2007/10/02)
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- Metal Complexes with Biological Important Ligands, XXVII. Palladium(II) and Platinum(II) Complexes with Aminomonosaccharides
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A series of dihalo palladium and platinum complexes X2PtL2 (X = Cl, I) with aminosugars L = 2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose, 1-O-methyl-2-amino-2-deoxy-4,6-O-benzyliden-α,β-D-glucopyranoside, 1-O-methyl-2-amino-2-deoxy-α,β-D-glucopyranoside, 6-amino-6-deoxy-1,2:3,4-di-O-isopropyliden-α-D-galactopyranose has been prepared and characterized by their IR, 1H and 13C NMR spectra.Monosaccharides and aminomonosaccharides have been attached to the complex via the carboxygroup of α-amino acid PtII complexes to give esters or amides with the monosaccharides as the alcohol or amine components, respectively. - Key words: Aminomonosaccharides, Palladium(II) Complexes, Platinum(II) Complexes
- Thiel, Gerhard,Beck, Wolfgang
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p. 1081 - 1093
(2007/10/02)
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