55682-57-0Relevant articles and documents
Oligosaccharide compound and its manufacture and its intermediate
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, (2018/04/14)
The purpose of the present invention is to provide an oligosaccharide with high versatility that can produce a protected sulfate oligosaccharide that can become a manufacturing intermediate of polysulfated hyaluronic acid, and to provide a manufacturing method therefor and an intermediate thereof. Position 2 amino groups in glucosamine, galactosamine, and the like can react with saccharide receptors having an electron attracting group such as glucuronic acid and protected sulfate groups, by using a saccharide donor protected by a specific protective group.
FGF RECEPTOR-ACTIVATING N-SULFATE OLIGOSACCHARIDES, PREPARATION THEREOF, AND THERAPEUTIC USE THEREOF
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, (2012/08/27)
The invention relates to FGF receptor-activating N-sulfate oligosaccharides having Formula (I), wherein R1, R4, R6, and R8 are —OSO3? or hydroxyl groups, R2 is an —O-alkyl group or a monosaccharide having Formula (II), R3 is a disaccharide having Formula (III), R5 is a disaccharide having Formula (IV), R7 is a hydroxyl group or a disaccharide having Formula (VI), and R9 is a hydroxyl or —O-alkyl group or a disaccharide having Formula (VII), where R10- is an —O-alkyl group. The invention further relates to the preparation of said oligosaccharides and to the therapeutic use thereof.
OLIGOSACCHARIDE COMPOUNDS FOR USE IN MOBILISING STEM CELLS
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Page/Page column 35, (2010/04/06)
A compound of the following formula or a salt, solvate or formula (I) and a pharmaceutical composition containing said compound. It concerns also its use in the treatment of cancer and/or of pathological angiogenesis and/or in promoting the mobilisation of stem cells, in particular hematopoietic stem cells.
Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate
Fairweather, Jon K.,Karoli, Tomislav,Liu, Ligong,Bytheway, Ian,Ferro, Vito
experimental part, p. 2394 - 2398 (2010/01/03)
A simple mimetic of a heparan sulfate disaccharide sequence that binds to the growth factors FGF-1 and FGF-2 was synthesized by coupling a 2-azido-2-deoxy-d-glucopyranosyl trichloroacetimidate donor with a 1,6-anhydro-2-azido-2-deoxy-β-d-glucopyranose acceptor. Both the donor and acceptor were obtained from a common intermediate readily obtained from d-glucal. Molecular docking calculations showed that the predicted locations of the disaccharide sulfo groups in the binding site of FGF-1 and FGF-2 are similar to the positions observed for co-crystallized heparin-derived oligosaccharides obtained from published crystal structures.
A modular strategy toward the synthesis of heparin-like oligosaccharides using monomeric building blocks in a sequential glycosylation strategy
Codee, Jeroen D. C.,Stubba, Bas,Schiattarella, Marialuisa,Overkleeft, Herman S.,Van Boeckel, Constant A. A.,Van Boom, Jacques H.,Van Der Marel, Gijsbert A.
, p. 3767 - 3773 (2007/10/03)
A novel flexible assembly strategy is described for the modular synthesis of heparin and heparan sulfates. The reported strategy uses monomeric building bocks to construct the oligosaccharide chain to attain a maximum degree of flexibility. In the assembly, 1-hydroxyl glucosazido- and 1-thio uronic acid donors are combined in a sequential glycosylation protocol using sulfonium triflate activator systems. The key 1-thio uronic acids were obtained in an efficient manner from diacetone glucose employing a chemo- and regioselective oxidation of partially protected glucose and idose thioglycosides.
α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose
Ganguli, Anjali R.S.,Coward, James K.
, p. 411 - 424 (2007/10/03)
The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an α-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the β-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of α,β arylglycosides.
Facile Preparation of 1,6-Anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose and Its 4-O-Substituted Derivatives
Sakairi, Nobuo,Takahashi, Shunya,Wang, Feng,Ueno, Yoshihito,Kuzuhara, Hiroyoshi
, p. 1756 - 1758 (2007/10/02)
Treatment of 1,6-anhydro-2,3-O-endo-benzylidene-β-D-mannopyranose derivatives with trimethylamine-borane (1/1)-aluminium chloride resulted in highly regioselective fission of the cyclic acetals to give the corresponding 2-O-unprotected-3-O-benzyl derivatives. Trifluoromethane-sulfonylation of these, followed by nucleophilic substitution, afforded 2-azido-2-deoxy derivatives in good yields.
An Expeditious and Stereocontrolled Preparation of 2-Azido-2-deoxy-β-D-glucopyranose Derivatives from D-Glucal
Tailler, Denis,Jaquinet, Jean-Claude,Noirot, Anne-Marie,Beau, Jean-Marie
, p. 3163 - 3164 (2007/10/02)
1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose has been prepared by a two-step procedure from D-glucal and transformed into precursors useful in the synthesis of oligosaccharides.
Regioselective De-O-benzylation with Lewis Acids
Hori, Hiroshi,Nishida, Yoshihiro,Ohrui, Hiroshi,Meguro, Hiroshi
, p. 1346 - 1353 (2007/10/02)
Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.
