101802-94-2Relevant academic research and scientific papers
2-Diphenylphosphinonyl-acetyl as a Remote Directing Group for the Highly Stereoselective Synthesis of β-Glycosides
Liu, Xianglai,Lin, Yetong,Liu, Ao,Sun, Qianhui,Sun, Huiyong,Xu, Peng,Li, Guolong,Song, Yingying,Xie, Weijia,Sun, Haopeng,Yu, Biao,Li, Wei
supporting information, p. 443 - 452 (2021/12/27)
The configuration of the anomeric glycosidic linkages is crucial for maintaining the biological functions and activities of carbohydrate molecules. However, their stereochemistry control in glycosylation represents one of the most challenging tasks in car
STABLE VACCINE AGAINST CLOSTRIDIUM DIFFICILE
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Page/Page column 134; 167, (2020/06/10)
The present invention relates to a synthetic saccharide of general formula (I) that is related to Clostridium difficile PS-II cell-surface polysaccharide and conjugate thereof. Said synthetic saccharide, said conjugate and pharmaceutical composition containing said synthetic saccharide or said conjugate are useful for prevention and/or treatment of diseases associated with Clostridium difficile. Furthermore, the synthetic saccharide of general formula (I) is useful as marker in immunological assays for detection of antibodies against Clostridium difficile bacteria.
Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy
Marianski, Mateusz,Mucha, Eike,Greis, Kim,Moon, Sooyeon,Pardo, Alonso,Kirschbaum, Carla,Thomas, Daniel A.,Meijer, Gerard,von Helden, Gert,Gilmore, Kerry,Seeberger, Peter H.,Pagel, Kevin
supporting information, p. 6166 - 6171 (2020/03/10)
The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.
HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS
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Paragraph 0302, (2016/05/10)
Glycosphingolipids (GSLs) compositions and methods for iNKT-independent induction of chemokines are disclosed.
Method for preventing cancer metastasis
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Page/Page column 20, (2015/11/10)
The present invention relates to the use of a specific family of glycerolipid compounds of formula (I) described in the detailed description or the manufacture of a medicament for the prevention or for the treatment of cancer metastasis.
HUMAN iNKT CELL ACTIVATION USING GLYCOLIPIDS WITH ALTERED GLYCOSYL GROUPS
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, (2015/03/16)
Glycosphingolipids (GSLs) bearing α-glucose (α-Glc) that preferentially stimulate human invariant NKT (iNKT) cells are provided. GSLs with α-glucose (α-Glc) that exhibit stronger induction in humans (but weaker in mice) of cytokines and chemokines and exp
A divergent approach to the synthesis of simplexides and congeners via a late-stage olefin cross-metathesis reaction
Li, Jiakun,Li, Wei,Yu, Biao
supporting information, p. 4971 - 4974 (2013/08/23)
Simplexides constitute a unique group of immunosuppressive glycolipids that demonstrate antiproliferative activities against activated T-cell lymphocytes via a unique non-cytotoxic inhibition. To investigate the structure-activity relationship of the varied long-chain secondary alcohols on simplexides, we developed an efficient and divergent route to the synthesis of simplexides and congeners, taking advantage of a late-stage olefin cross-metathesis reaction.
Regioselective acetolysis of highly O-benzylated carbohydrates promoted by iodine or an iodine/silane combined reagent: Use of isopropenyl acetate as an alternative to acetic anhydride
Giordano, Maddalena,Iadonisi, Alfonso,Pastore, Antonello
, p. 3137 - 3147 (2013/06/27)
Regioselective acetolytic de-O-benzylation of poly-O-benzylated sugars can be triggered by the activation of isopropenyl acetate (IPA) with either an iodine/silane combined reagent or iodine alone. Unlike other known acetolysis procedures, the protocols p
Low-concentration 12-trans β-selective glycosylation strategy and its applications in oligosaccharide synthesis
Chao, Chin-Sheng,Li, Chen-Wei,Chen, Min-Chun,Chang, Shih-Sheng,Mong, Kwok-Kong Tony
supporting information; experimental part, p. 10972 - 10982 (2010/04/30)
This study develops an operationally easy, efficient, and general 1,2-trans β-selective glycosylation reaction that proceeds in the absence of a C2 acyl function. This process employs chemically stable thioglycosyl donors and low substrate concentrations to achieve excellent β-selectivities in glycosylation reactions. This method is widely applicable to a range of glycosyl substrates irrespective of their structures and hydroxyl-protecting functions. This low-concentration 1,2-trans β-selective glycosylation in carbohydrate chemistry removes the restriction of using highly reactive thioglycosides to construct 1,2-trans β-glycosidic bonds. This is beneficial to the design of new strategies for oligosaccharide synthesis, as illustrated in the preparation of the biologically relevant β-(1-6)-glucan trisaccharide, β-linked Gb3 and isoGb3 derivatives.
A short access to the macrocyclic core of cycloviracin and glucolipsin
Bailliez, Vincent,Figueiredo, Renata M. de,Olesker, Alain,Cleophax, Jeannine
, p. 9151 - 9154 (2007/10/03)
The macrocyclic core of cycloviracin and glucolipsin has been synthesised in ten steps from levoglucosan and (S)-(-)-dimethyl malate. The limited number of steps to obtain this macrolide makes it a valuable procedure for the synthesis of analogues of cycl
