66252-72-0Relevant academic research and scientific papers
Cholesteryl glucosides signal through the carbohydrate recognition domain of the macrophage inducible C-type lectin (mincle)
Timmer, Mattie S. M.,Teunissen, Thomas J.,Kodar, Kristel,Foster, Amy J.,Yamasaki, Sho,Stocker, Bridget L.
, p. 2198 - 2202 (2021)
Cholesteryl α-d-glucosides (αGCs) are unique metabolic products of the cancer-causing human pathogenHelicobacter pylori.Viasignalling through the Macrophage inducible C-type lectin (Mincle) and the induction of a pro-inflammatory response, they are thought to play a role in the development of gastric atrophy. Herein, we prepared the first library of steryld-glucosides and determined that they preferentially signal through the carbohydrate recognition domain of human Mincle, rather than the amino acid consensus motif. Lipidated steryld-glucosides exhibited enhanced Mincle agonist activity, with C18 cholesteryl 6-O-acyl-α-d-glucoside (2c) being the most potent activator of human monocytes. Despite exhibiting strong Mincle signalling, sito- (5b) and stigmasterol glycosides (6b) led to a poor inflammatory response in primary cells, suggesting that Mincle is a potential therapeutic target for preventingH. pylori-mediated inflammation and cancer.
Bismuth(iii) triflate as a novel and efficient activator for glycosyl halides
Steber, Hayley B.,Singh, Yashapal,Demchenko, Alexei V.
, p. 3220 - 3233 (2021/04/21)
Presented herein is the discovery that bismuth(iii) trifluoromethanesulfonate (Bi(OTf)3) is an effective catalyst for the activation of glycosyl bromides and glycosyl chlorides. The key objective for the development of this methodology is to em
A Mild Glycosylation Protocol with Glycosyl 1-Methylimidazole-2-carboxylates as Donors
Chen, Jianpeng,Tang, Yu,Yu, Biao
, p. 4333 - 4344 (2021/07/26)
A mild glycosylation protocol is developed by using glycosyl 1-methylimidazole-2-carboxylates. Such a glycosylation can be promoted by a series of metal triflates and triflimides, especially Cu(OTf)2. The reaction is initiated by activation of
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
Gold(I)-Catalyzed Intermolecular Rearrangement Reaction of Glycosyl Alkynoic β-Ketoesters for the Synthesis of 4- O-Glycosylated 2-Pyrones
Liu, Rongkun,Li, Xiaoqian,Li, Xiaona,Wang, Jiazhe,Yang, You
, p. 14141 - 14150 (2019/10/17)
A new gold(I)-catalyzed rearrangement reaction with glycosyl alkynoic β-ketoesters as substrates is developed. The rearrangement reactions under the catalysis of PPh3AuOTf proceeded smoothly to afford a range of 4-O-glycosylated 2-pyrones. Base
Homogeneous Gold-Catalyzed Glycosylations in Continuous Flow
Matthies, Stefan,McQuade, D. Tyler,Seeberger, Peter H.
supporting information, p. 3670 - 3673 (2015/08/18)
The use of versatile alkynyl-building blocks that are activated by gold(I)-catalysis is demonstrated to efficiently generate a variety of glycosides in continuous flow. The application of a continuous flow setting to gold(I)-catalyzed glycosylations enables very short reaction times and excellent control of the reaction conditions.
Photoinduced C-S Bond Cleavage of Thioglycosides and Glycosylation
Mao, Run-Ze,Guo, Fan,Xiong, De-Cai,Li, Qin,Duan, Jinyou,Ye, Xin-Shan
supporting information, p. 5606 - 5609 (2015/12/01)
A glycosyl coupling reaction via photoinduced direct activation of thioglycosides and subsequent O-glycosylation in the absence of photosensitizer was developed for the first time. This reaction underwent a selectively homolytic cleavage of a C-S bond to generate a glycosyl radical, which was oxidized to an oxacarbenium ion by Cu(OTf)2, and a sequential O-glycosylation. A wide range of glycosides were synthesized in moderate to excellent yield using sugars, amino acids, or cholesterol as the acceptors.
ortho-(Methyltosylaminoethynyl)benzyl glycosides as new glycosyl donors for latent-active glycosylation
Chen, Xiaoping,Shen, Dacheng,Wang, Qiaoling,Yang, You,Yu, Biao
supporting information, p. 13957 - 13960 (2015/09/07)
A new glycosylation protocol employing ortho-(methyltosylaminoethynyl)benzyl glycosides as glycosyl donors and TMSOTf as the catalyst is disclosed. These donors can be readily prepared from the corresponding 'latent' ortho-iodobenzyl glycosides via a Sonogashira coupling, thus providing a new approach for the 'latent-active' synthesis of glycans.
Studies of S -But-3-ynyl and gem -dimethyl S -But-3-ynyl thioglycoside donors in gold-catalyzed glycosylations
Adhikari, Surya,Li, Xiaohua,Zhu, Jianglong
, p. 336 - 359 (2013/10/08)
Gold-catalyzed glycosylation using S-but-3-ynyl and gem-dimethyl S-but-3-ynyl thioglycoside donors has been investigated for the synthesis of various types of complex oligosaccharides. It was found that 2,2-dimethyl S-but-3-ynyl thioglycoside donors are m
Glycosylation of alcohols using glycosyl boranophosphates as glycosyl donors
Tatsumi, Shiro,Matsumura, Fumiko,Oka, Natsuhisa,Wada, Takeshi
supporting information, p. 3731 - 3734 (2013/07/05)
A novel glycosylation that uses glycosyl boranophosphate triesters as glycosyl donors and trityl cation (Tr+) as an activator was developed. Two types of reactions were studied: (1) the boranophosphate triester was activated with TrNTf2 to react with an alcohol and (2) O-trityl ethers worked as both glycosyl acceptors and Tr+ sources. The latter gave better results and the desired O-glycosylation products were rapidly generated and isolated in moderate to good yields.
