6619-02-9Relevant academic research and scientific papers
Ultrasonication-Assisted Synthesis of a d-Glucosamine-Based β-CD Inclusion Complex and Its Application as an Aqueous Heterogeneous Organocatalytic System
Rani, Dhiraj,Sethi, Aaftaab,Kaur, Khushwinder,Agarwal, Jyoti
, p. 9548 - 9557 (2020/09/09)
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
New phosphine-imine and phosphine-amine ligands derived from D-gluco-, D-galacto- and D-allosamine in Pd-catalysed asymmetric allylic alkylation
Szulc, Izabela,Ko?odziuk, Robert,Zawisza, Anna
, p. 1476 - 1485 (2018/02/19)
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.
D-Glucosamine as a novel chiral auxiliary for the stereoselective synthesis of P-stereogenic phosphine oxides
D'Onofrio,Copey,Jean-Gérard,Goux-Henry,Pilet,Andrioletti,Framery
supporting information, p. 9029 - 9034 (2015/09/01)
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
Diaminohexopyranosides as ligands in half-sandwich ruthenium(II), rhodium(III), and iridium(III) complexes
B?ge, Matthias,Fowelin, Christian,Bednarski, Patrick,Heck, Jürgen
supporting information, p. 1507 - 1521 (2015/05/13)
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.
3- and 4-uloses derived from N-acetyl- D -glucosamine: A unique pair of complementary organocatalysts for asymmetric epoxidation of alkenes
Schoeberl, Christof,Jaeger, Volker
supporting information; experimental part, p. 790 - 796 (2012/05/04)
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
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
Tatina, Madhubabu,Yousuf, Syed Khalid,Mukherjee, Debaraj
supporting information; experimental part, p. 5357 - 5360 (2012/07/30)
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.
Glucosamine-based primary amines as organocatalysts for the asymmetric aldol reaction
Agarwal, Jyoti,Peddinti, Rama Krishna
scheme or table, p. 3502 - 3505 (2011/06/21)
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
Synthesis and characterization of d-glucosamine-derived low molecular weight gelators
Goyal, Navneet,Cheuk, Sherwin,Wang, Guijun
supporting information; experimental part, p. 5962 - 5971 (2010/09/18)
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
Accessible sugars as asymmetric olefin epoxidation organocatalysts: Glucosaminide ketones in the synthesis of terminal epoxides
Boutureira, Omar,McGouran, Joanna F.,Stafford, Robert L.,Emmerson, Daniel P. G.,Davis, Benjamin G.
supporting information; experimental part, p. 4285 - 4288 (2009/12/05)
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.
A 1-acetamido derivative of 6-epi-valienamine: An inhibitor of a diverse group of β-N-acetylglucosaminidases
Scaffidi, Adrian,Stubbs, Keith A.,Dennis, Rebecca J.,Taylor, Edward J.,Davies, Gideon J.,Vocadlo, David J.,Stick, Robert V.
, p. 3013 - 3019 (2008/04/01)
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.
