114682-36-9Relevant academic research and scientific papers
Synthesis and inhibition of α-glucosidase of methyl glycyrrhetinate glycosides
Zhang, Wei,Wang, He-Ying,Wang, Huai-Xu,Zhu, Zhen-Yuan
, p. 1874 - 1880 (2019/07/22)
The synthesis of the methyl glycyrrhetinate glycosides and inhibition of α-glucosidase were studied. The carboxyl group of glycyrrhetinic acid was methylated, and glucose and galactose were introduced into the hydroxyl group to obtain compounds 7 and 12.
Preparation method of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents
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, (2020/07/29)
The invention relates to a synthetic route of glycyrrhetinic acid glucoside and application of glycyrrhetinic acid glucoside in sweetening agents, and belongs to the field of synthesis of novel sweetening agents. The novel sweetening agent with higher swe
Synthesis of Glycosyl Chlorides and Bromides by Chelation Assisted Activation of Picolinic Esters under Mild Neutral Conditions
Balzer, Paul G.,Blaszczyk, Stephanie A.,Duan, Xiyan,Ma, Zhi-Xiong,Simmons, Christopher J.,Stevens, Christopher M.,Tang, Weiping,Wang, Hao-Yuan,Wen, Peng,Ye, Wenjing,Yin, Dan
supporting information, (2020/02/28)
A general method has been developed for the formation of glycosyl chlorides and bromides from picolinic esters under mild and neutral conditions. Benchtop stable picolinic esters are activated by a copper(II) halide species to afford the corresponding products in high yields with a traceless leaving group. Rare β glycosyl chlorides are accessible via this route through neighboring group participation. Additionally, glycosyl chlorides with labile protecting groups previously not easily accessible can be prepared.
Koenigs–Knorr Glycosylation Reaction Catalyzed by Trimethylsilyl Trifluoromethanesulfonate
Singh, Yashapal,Demchenko, Alexei V.
supporting information, p. 1461 - 1465 (2019/01/04)
The discovery that traditional silver(I)-oxide-promoted glycosidations of glycosyl bromides (Koenigs–Knorr reaction) can be greatly accelerated in the presence of catalytic trimethylsilyl trifluoromethanesulfonate (TMSOTf) is reported. The reaction conditions are very mild that allowed for maintaining a practically neutral pH and, at the same time, providing high rates and excellent glycosylation yields. In addition, unusual reactivity trends among a series of differentially protected glycosyl bromides were documented. In particular, benzoylated α-bromides were much more reactive than their benzylated counterparts under these conditions.
Regenerative Glycosylation
Singh, Yashapal,Wang, Tinghua,Geringer, Scott A.,Stine, Keith J.,Demchenko, Alexei V.
, p. 374 - 381 (2018/01/01)
Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.
3 - monosaccharide acid oxygen glucoside oleanolic alkane type and wusu alkane triterpene saponin derivative and its preparation method and application
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Paragraph 0035; 0037; 0113, (2017/08/25)
The invention discloses a 3-monouronic acid o-glycoside oleanane type and ursane type triterpenoid saponin derivative. The derivative has a structural formula as shown in the specification, wherein R4 is one of H atom, alkyl containing 1-10 carbons, alkyl
Stereoselective Epimerizations of Glycosyl Thiols
Doyle, Lisa M.,O'Sullivan, Shane,Di Salvo, Claudia,McKinney, Michelle,McArdle, Patrick,Murphy, Paul V.
, p. 5802 - 5805 (2017/11/10)
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while SnCl4 promoted their axial-to-equatorial epimerization. The method included application for stereoselective β-d-manno- and β-l-rhamnopyranosyl thiol formation. Complex formation explains the equatorial preference when using SnCl4, whereas TiCl4 can shift the equilibrium toward the 1,2-cis thiol via 1,3-oxathiolane formation.
Sites for dynamic protein-carbohydrate interactions of O- and C-linked mannosides on the E. coli FimH adhesin
Touaibia, Mohamed,Krammer, Eva-Maria,Shiao, Tze C.,Yamakawa, Nao,Wang, Qingan,Glinschert, Anja,Papadopoulos, Alex,Mousavifar, Leila,Maes, Emmanuel,Oscarson, Stefan,Vergoten, Gerard,Lensink, Marc F.,Roy, René,Bouckaert, Julie
, (2017/08/30)
Antagonists of the Escherichia coli type-1 fimbrial adhesin FimH are recognized as attractive alternatives for antibiotic therapies and prophylaxes against acute and recurrent bacterial infections. In this study α-D-mannopyranosides O- or C-linked with an
DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO
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Paragraph 0408; 0409, (2013/06/04)
The present invention relates to methods for synthesizing compounds of formula I or pharmaceutically acceptable salts thereof: (I) wherein each of X, Alk, and W are as defined and described herein.
DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO
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Paragraph 0634; 0635, (2013/07/31)
The present invention relates to methods for synthesizing compounds of formula I or pharmaceutically acceptable salts thereof: I wherein each of X, Alk1, Alk2, and W are as defined and described herein.
