150412-78-5Relevant academic research and scientific papers
HClO4-SiO2 catalyzed glycosylation using sugar trichloroacetimidates as glycosyl donors
Du, Yuguo,Wei, Guohua,Cheng, Shuihong,Hua, Yuxia,Linhardt, Robert J.
, p. 307 - 310 (2006)
Silica-supported perchloric acid (HClO4-SiO2) has been used as an efficient promoter, as a replacement of TMSOTf, in various glycosylation reactions using sugar trichloroacetimidates as glycosyl donors. Operational simplicity, econom
Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors
Li, Xiaona,Li, Chenyu,Liu, Rongkun,Wang, Jiazhe,Wang, Zixuan,Chen, Yan,Yang, You
supporting information, p. 9693 - 9698 (2019/11/29)
A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wid
Facile synthesis of triterpenoid saponins bearing β-Glu/Gal-(1→3) -β-GluA methyl ester and their cytotoxic activities
Gao, Jian,Li, Xia,Gu, Guofeng,Liu, Shanshan,Cui, Min,Lou, Hong-Xiang
scheme or table, p. 2396 - 2400 (2012/05/19)
Convenient synthetic strategy toward spinasaponin A methyl ester 1 and calenduloside G methyl ester 2, two natural oleanane-type triterpenoid saponins bearing an unique β-d-glucosyl/galactosyl-(1→3)-β-d-glucuronic acid methyl ester disaccharide moiety, was established. Based on this facile approach, four structurally modified congeners 3-6 with ursolic acid and glycyrrhetinic acid as aglycones were efficiently synthesized. MTT assay revealed the cytotoxicities against cancer cells of the synthesized saponins were varied with the change of aglycones and sugar units. Saponin 2 possessing the most potent cytotoxic effects could induce apoptosis of MCF-7 cells, which was detected by confocal micrographs using DAPI staining and flow cytometry using Annexin V and PI double staining. Furthermore, 2-induced apoptosis in MCF-7 cells was associated with ROS generation and loss of the mitochondria membrane potential (Δψm).
A KIND OF OLIGOSACCHARIDES, THEIR SULFATES AND DENDRIMERS, AND THE USES OF THESE COMPOUNDS
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Page 5-6, (2010/02/06)
This invention involves a type of oligosaccharides and its sulfate derivatives. The backbone of the oligosaccharides consists of 3 to 14 sugar residues, while the side chains contain 0 to 4 sugar residues. There is at least one 1→3α linkage in the backbon
Highly efficient syntheses of the phytoalexin-elicitor active β- (1→3)-branched β-(1→6)-linked heptaglucose and its dodecyl glycoside
Yi, Yuetao,Zhou, Zhongxuan,Ning, Jun,Kong, Fanzuo,Li, Jianqiang
, p. 491 - 496 (2007/10/03)
A highly efficient method for the synthesis of 3,6-branched gluco-oligosaccharides was developed by using 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate, and 6-O-acetyl-2,3,4-tri-O-benzoyl-α-
Synthesis of β-(1→6)-branched β-(1→3) glucohexaose and its analogues containing an α-(1→3) linked bond with antitumor activity
Ning, Jun,Zhang, Wenhui,Yi, Yuetao,Yang, Guangbin,Wu, Zhikui,Yi, Jie,Kong, Fanzuo
, p. 2193 - 2203 (2007/10/03)
A β-(1→6)-branched β-(1→3)-glucohexaose, present in many biologically active polysaccharides from traditionally herbal medicines such as Ganoderma lucidum, Schizophyllum commune and Lentinus edodes, was synthesized as its lauryl glycoside 32, and its anal
Synthesis of two isomeric pentasaccharides, the possible repeating unit of the beta-glucan from the micro fungus Epicoccum nigrum Ehrenb. ex Schlecht.
Zeng, Ying,Zhang, Wenhui,Ning, Jun,Kong, Fanzuo
, p. 2383 - 2391 (2007/10/03)
Two isomeric pentasaccharides, beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->6)]-beta-D-Glcp (I) and beta-D-Glcp-(1-->6)-beta-D-Glcp-(1-->3)-[beta-D-Glcp-(1-->3)-beta-D-Glcp-(1-->6)]-beta-D-Glcp (II), the possible repeati
A general strategy for the synthesis of 3,6-branched gluco-oligosaccharides: Facile synthesis of the phytoalexin elicitor oligosaccharides
Gómez, Ana M.,Moreno, Eduardo,Valverde, Serafín,López, J.Cristóbal
, p. 5545 - 5549 (2007/10/03)
A general method for the synthesis of 3,6-branched gluco-oligosaccharides has been developed. As a typical example of the method, the synthesis of the glucohexatose phytoalexin elicitor on a large scale was achieved via coupling of a trisaccharide donor with a trisaccharide acceptor. The donor and acceptor were prepared easily from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate, and 6-O-acetyl-2,3,4-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate in a regio- and stereoselective manner. Higher oligosaccharides of the elicitor including the hepta-, nona-, dodeca- and tetradecasaccharides have also been readily synthesized by this strategy.
A stereoselective glycosidation using thioglycosides, activation by combination of N-bromosuccinimide and strong acid salts
Fukase, Koichi,Hasuoka, Atsushi,Kinoshita, Ikuko,Aoki, Yutaka,Kusumoto, Shoichi
, p. 4923 - 4932 (2007/10/02)
A stereoselective glycosidation with thioglycosides was effected under mild and neutral conditions by combined use of N-bromosuccinimide (NBS) and a catalytic amount of various strong acid salts. A combination of NBS with Ph2IOTf, Bu4NOTf, or Bu4NClO4 was advantageous for β-selective glucosidation with 2-O-acylated or 2-O-benzylated donors by virtue of either the neighboring group participation or the known solvent effect of nitrile, respectively. α-Selective glucosidation was effected by the use of a 2-O-benzylated donor in the presence of LiClO4 or LiNO3 as a catalyst in ether. Addition of silica gel to the reaction mixture increased both the α-selectivity and reaction rate.
A novel method for activation of thioglycosides, combination of N-bromosuccinimide and triflic acid salts
Fukase, Koichi,Hasuoka, Atsushi,Kusumoto, Shoichi
, p. 2187 - 2190 (2007/10/02)
A combination of N-bromosuccinimide (NBS) with tetrabutylammonium triflate (Bu4NOTf) or diphenyliodonium triflate (Ph2IOTf) effectively activates thioglycosides to promote facile glycosidation with various glycosyl acceptors in good
