- Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegenerative activity on bovine and human cartilage explants
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(d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis (OA), a chronic and degenerative articular joint disease. In our preceding paper, a series of novel O-6 phosphate N-acetyl (d)-glucosamine prod
- Serpi, Michaela,Bibbo, Rita,Rat, Stephanie,Roberts, Helen,Hughes, Claire,Caterson, Bruce,Alcaraz, María José,Gibert, Anna Torrent,Verson, Carlos Raul Alaez,McGuigan, Christopher
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supporting information; experimental part
p. 4629 - 4639
(2012/07/01)
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- Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O- benzylidene-2-deoxy-d-glucopyranose by anomeric O-alkylation
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The reaction of a partially protected 1-hydroxy derivative of N-acetyl-d-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali me
- Pertel, Sergey S.,Gorkunenko, Oksana A.,Kakayan, Elena S.,Chirva, Vasily Ja.
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body text
p. 685 - 688
(2011/04/26)
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- PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DI- OR OLIGO-SACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF
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The present invention relates to a process for the synthesis of L-fucosyl di- or oligosaccharides and their novel 2,3,4-tri-O-benzyl-fucosyl synthetic intermediates derivatives of easy crystallization. In particular the present invention relates to a proc
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Page/Page column 15
(2011/10/13)
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- PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DL- OR OLIGOSACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF
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The present invention relates to a process for the synthesis of L-fυcosyl di- or oligosaccharides and their novel 2,3,4-tri-O-benzyl-fucosyl synthetic intermediates derivatives of easy crystallization. In particular the present invention relates to a process applicable to industrial scale for the synthesis of 2'O-fucosyl lactose.
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Page/Page column 37-38
(2010/08/05)
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- Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives
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We report herein a bacterial N-acetylhexosamine kinase, NahK, with broad substrate specificity towards structurally modified GalNAc analogues, and the production of a GalNAc-1-phosphate library using this kinase.
- Cai, Li,Guan, Wanyi,Wang, Wenjun,Zhao, Wei,Kitaoka, Motomitsu,Shen, Jie,O'Neil, Crystal,Wang, Peng George
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supporting information; experimental part
p. 5433 - 5435
(2010/05/02)
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- Synthesis and biological evaluation of a lipid A derivative that contains an aminogluconate moiety
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A highly convergent strategy for the synthesis of several derivatives of the lipid A of Rhizobium sin-1 has been developed. The synthetic derivatives are 2-aminogluconate 3 and 2-aminogluconolactone 4, both of which lack C-3 acylation. These derivatives w
- Santhanam, Balaji,Wolfert, Margreet A.,Moore, James N.,Boons, Geert-Jan
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p. 4798 - 4807
(2007/10/03)
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- Palladium-catalysed asymmetric allylic alkylation using new chiral phosphinite-nitrogen ligands derived from D-glucosamine
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Novel phosphinite-nitrogen chiral ligands synthesized from D-glucosamine furnish a high level of enantiomeric excess (up to 96% ee] in palladium-catalysed allylic alkylation.
- Yonehara, Koji,Hashizume, Tomohiro,Mori, Kenji,Obe, Kouichi,Uemura, Sakae
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p. 415 - 416
(2007/10/03)
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- Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinite-oxazoline ligands derived from D-glucosamine
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Novel 2-alkyl- or 2-aryl-4,5-(4,6-O-benzylidene-3-O-(diphenylphosphino)- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazolines (5a-f) have been prepared from D-glucosamine hydrochloride. They work effectively as chiral ligands and provide a high level of enantiomeric excess in palladium-catalyzed allylic alkylation and amination reactions. The allylic alkylation of 1,3-diphenyl-3- acetoxyprop-1-ene with dimethyl malonate proceeds smoothly in the presence of 0.25 mol % [Pd(η3C3H5)Cl]2 and the chiral ligand 5a having the smallest substituent on oxazoline at 0 °C within 6 h to furnish the highest enantiomeric excess (96% ee). The ligand 5a is also effective for the Pd- catalyzed amination of ethyl 1,3-diphenylprop-2-enyl carbonate, leading to the corresponding allylic amine in 94% ee. The full scope and limitations using ligands 5a-f in the allylic substitution reactions are described.
- Yonehara, Koji,Hashizume, Tomohiro,Mori, Kenji,Ohe, Kouichi,Uemura, Sakae
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p. 9374 - 9380
(2007/10/03)
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