627466-84-6Relevant articles and documents
Carbon tetrachloride-free allylic halogenation-mediated glycosylations of allyl glycosides
Das, Anupama,Jayaraman, Narayanaswamy
, p. 9318 - 9325 (2021/11/13)
The allylic bromination of allyl glycosides is conducted using NBS/AIBN reagents in (EtO)2CO and PhCF3 solutions, without using CCl4 as a solvent. The activated mixed halo-allyl glycosides led to glycosylations, mediated by a triflate, in a latent-active
Synthesis of the hexasaccharide from Trypanosoma cruzi mucins with the Galp(1?→?2)Galf unit constructed with a superarmed thiogalactopyranosyl donor
Kashiwagi, Gustavo A.,Cori, Carmen R.,de Lederkremer, Rosa M.,Gallo-Rodriguez, Carola
, (2019/07/05)
Hexasaccharide β-D-Galp-(1→ 2)-[β-D-Galp-(1 → 3)]-β-D-Galp-(1 → 6)-[β-D-Galp-(1 → 2)-β-D-Galf-(1 → 4)]-D-GlcNAc (1) was found O-linked in mucins of Trypanosoma cruzi epimastigotes and metacyclic trypomatigotes. Studies on the biological pathways and functionalities of the mucin oligosaccharides are prompted in order to understand the interactions of these molecules with the insect host. Trisaccharide constituent β-D-Galp-(1 → 2)-β-D-Galf-(1 → 4)-D-GlcNAc was constructed from the reducing to the non-reducing end. We discuss the difficulties to introduce a Galp unit at the O-2 position of a partially protected galactofuranosyl unit which were overcome using an anchimerically superarmed donor. By this route and employing a [3 + 3] nitrilium convergent approach hexasaccharide 1 was synthesized in moderate yield.
ENDOSOMAL CLEAVABLE LINKERS
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, (2018/08/20)
The present disclosure relates generally to cleavable linkers and uses thereof.
The dehydroepiandrosterone and dehydroepiandrosterone alkone glycosylation derivative and its preparation method and application
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Paragraph 0041; 0046; 0049, (2017/04/28)
The invention discloses epiandrosterone glycosylation derivatives and dehydrogenated epiandrosterone glycosylation derivatives, and a preparation method thereof. The preparation method comprises the following steps: respectively carrying out coupling reac
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; 0038; 0059, (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
A new method for selective deprotection of anomeric N,O -dimethylhydroxylamine promoted by TMSCl
Huang, Shengjun,Liao, Jun,Zhao, Qingjie,Chai, Xiaoyun,Wang, Baogang,Yu, Shichong,Wu, Qiuye
, p. 158 - 168 (2013/03/29)
TMSCl was shown to be an efficient reagent for selective deprotection of the anomeric position protected as N,O-dimethylhydroxylamine glycoside. This deprotection condition was proved to be compatible with a number of protecting groups, such as the TBDPS, acetyl, benzyl, benzylidene, and benzoyl groups.Copyright Taylor and Francis Group, LLC.
Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
Wang, Ying-Hsin,Yeh, Hsien-Wei,Wang, Hsiao-Wen,Yu, Chia-Chun,Guh, Jih-Hwa,Liu, Der-Zen,Liang, Pi-Hui
, p. 118 - 135 (2013/07/27)
Naturally occurring spirostanol saponins bear a chacotriose, α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→4)] -β-d-glucopyranose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2′ and/or 4′ positions of chacotriose is described and the structure-activity relationships of the glycone part at 3-OH of chlorogenin investigated. These compounds were found to be weakly-cytotoxic toward leukemia cell lines CCRF and HL-20, indicating that the chacotriose moiety is important for anticancer activity.
Trichloroisocyanuric acid (TCCA): An efficient green reagent for activation of thioglycosides toward hydrolysis
Basu, Nabamita,Maity, Sajal Kumar,Chaudhury, Aritra,Ghosh, Rina
, p. 10 - 13 (2013/04/24)
Trichloroisocyanuric acid (TCCA), an inexpensive, commercially available, and non-toxic reagent has been used for the activation of thioglycosides toward their hydrolysis to the corresponding hemiacetals in high to excellent yields. The methodology provides a mild reaction condition for dealing with compounds containing acid sensitive functional groups.
Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicine Cordyceps sinensis
Zhu, Zhen-Yuan,Yao, Qiang,Liu, Yang,Si, Chuan-Ling,Chen, Jing,Liu, Nian,Lian, Hong-Yu,Ding, Li-Na,Zhang, Yong-Min
, p. 429 - 435 (2012/10/07)
Ergosterol 3-O-β-d-glucopyranoside (1a) and ergosterol 3-O-d-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by 1H, 13C NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.
Mitochondrial affinity of guanidine-rich molecular transporters built on monosaccharide scaffolds: Stereochemistry and lipophilicity
Lee, Woo Sirl,Kim, Wanil,Kim, Kyong-Tai,Chung, Sung-Kee
, p. 2286 - 2300 (2012/06/16)
We synthesized eight G8 molecular transporters (MTs) based on 4 different monosaccharide scaffolds, and studied their biological properties with a special focus on possible mitochondrial targeting and tissue selectivity. The mitochondrial affinity of these MTs was found to be clearly related to the scaffold stereochemistry and also tenuously with the lipophilicity. It may be suggested that in the practical delivery strategy of drugs for the brain and mitochondrial diseases the BBB permeability and mitochondrial affinity should be considered as key parameters, and that an enhanced mitochondrial affinity appears possible by further research on the structure-property relationship of guanidine-rich molecular transporters.