82659-52-7Relevant academic research and scientific papers
8-(Methyltosylaminoethynyl)-1-naphthyl (MTAEN) Glycosides: Potent Donors in Glycosides Synthesis
Zhou, Si-Yu,Hu, Xin-Ping,Liu, Hui-Juan,Zhang, Qing-Ju,Liao, Jin-Xi,Tu, Yuan-Hong,Sun, Jian-Song
supporting information, p. 653 - 657 (2022/01/20)
With 8-(methyltosylaminoethynyl)-1-naphthyl (MTAEN) glycoside as donors, a novel and efficient glycosylation protocol has been established. The MTAEN glycosylation protocol exhibits the merits of shelf-stable donors, mild catalytic promotion conditions, considerably extended substrate scope encompassing both free alcohols, silylated alcohols, nucleobases, primary amides, and C-type nucleophile acceptors, and applicability to various one-pot strategies for highly efficient synthesis of oligosaccharides, such as orthogonal one-pot, single-catalyst one-pot, and acceptor reactivity-controlled one-pot strategies.
A protecting group-free approach for synthesizingC-glycosides through glycosyl dithiocarbamates
Li, Gefei,Noguchi, Masato,Arisaka, Genki,Tanaka, Yuuki,Shoda, Shin-Ichiro
supporting information, p. 3134 - 3138 (2021/04/21)
The first protection/deprotection-free process for radicalC-glycosylation has been achieved through one-step preparable glycosyl dithiocarbamates (GDTCs). The Giese-type reaction and radical allylation of unprotected GDTCs were successfully performed to obtain the corresponding α-C-glycosides stereoselectively under mild reaction conditions.
Carbon glycoside glycosylated tetravalent platinum compound as well as synthesis method and application thereof
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, (2021/07/08)
The invention provides a carbon glycoside glycosylated tetravalent platinum compound, a synthesis method and application thereof. R1 and R2 are independently C1-C4 lower alkanes, R3 is glucose, galactose, mannose and ribose, different sugars are used as raw materials, and a series of carbon glycoside glycosylated tetravalent platinum compounds are synthesized through protection and deprotection reaction and metallization reaction of the sugars. The synthesis method is simple, the used raw materials are cheap and easy to obtain, the glycosylated tetravalent platinum compound has the capacity of targeting glucose transporter protein and has potential application value in the field of cancer treatment, introduction of a C-glucosidic bond enables the series of compounds to have the capacity of resisting hydrolysis of beta-glucosidase, and the compound is expected to be applied to the field of oral antitumor drugs.
Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group
Tang, Weiping,Ye, Wenjing,Stevens, Christopher M.,Wen, Peng,Simmons, Christopher J.
, p. 16218 - 16225 (2021/01/19)
C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.
C -Glycosylation enabled by N -(glycosyloxy)acetamides
Li, Bo-Han,Li, Tian,Liu, Meng,Liu, Miao,Wu, Xia,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 3043 - 3046 (2020/05/08)
The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.
CuBr2-catalyzed diastereoselective allylation: Total synthesis of decytospolides A and B and their C6-epimers
Choudhury, Utkal Mani,Mallampudi, N. Arjunreddy,Mohapatra, Debendra K.,Padhi, Birakishore,Reddy, G. Sudhakar
, p. 2685 - 2695 (2020/04/17)
An efficient CuBr2-catalyzed diastereoselective allylation of a cyclic hemiacetal with allyltrimethylsilane as a nucleophile has been developed. The protocol offers a cost effective, protecting group tolerant, and operationally simple approach to 2,6-trans-disubstituted tetrahydropyran with excellent diastereoselectivity. Furthermore, the application of this methodology has been demonstrated in the total synthesis of decytospolides A and B and their C6-epimers.
Glucose-conjugated platinum(IV) complexes as tumor-targeting agents: design, synthesis and biological evaluation
Wang, Haifeng,Yang, Xiande,Zhao, Caili,Wang, Peng George,Wang, Xin
, p. 1639 - 1645 (2019/03/08)
A new series of glucose-conjugated Pt(IV) complexes that target tumor-specific glucose transporters (GLUTs) was designed, synthesized, and evaluated for their anticancer activities. All six compounds, namely, A1-A6, exhibited increased cytotoxicity that w
Nucleofuge Generating Glycosidations by the Remote Activation of Hydroxybenzotriazolyl Glycosides
Neralkar, Mahesh,Mishra, Bijoyananda,Hotha, Srinivas
, p. 11494 - 11504 (2017/11/10)
Hydroxybenzotriazole is routinely used in peptide chemistry for reducing racemization due to the increased reactivity. In this article, very stable hydroxybenzotriazolyl glucosides were identified to undergo glycosidation. The reaction was hypothesized to go through the remote activation by the Tf2O at the N3-site of HOBt followed by the extrusion of the oxocarbenium ion that was attacked by the glycosyl acceptor. Further, equilibration of the zwitterionic benzotriazolyl species makes the leaving group noncompetitive and generates the nucleofuge that has been reconverted to the glycosyl donor. The reaction is mild, high yielding, fast and suitable for donors containing both C2-ethers and C2-esters as well. The regenerative-donor glycosidation strategy is promising as it enables us to regenerate the glycosyl donor for further utilization. The utility of the methodology for the oligosaccharide synthesis was demonstrated by the successful synthesis of the branched pentamannan core of the HIV1-gp120 complex.
Synthesis and revised stereochemical assignment of C-allyl glucopyranosides and derivatives
Petry, Nicolas,Vucko, Timothé,Collet, Charlotte,Lamandé-Langle, Sandrine,Pellegrini-Mo?se, Nadia,Chrétien, Fran?oise
supporting information, p. 61 - 64 (2017/04/19)
α- and β-C-allylglucopyranosides and hydroxy-, bromo- and azido-derivatives were prepared through allylation at C-1 of methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside or 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose and subsequent chemical modificatio
Understanding multivalent effects in glycosidase inhibition using: C -glycoside click clusters as molecular probes
Stauffert, Fabien,Bodlenner, Anne,Nguyet Trinh, Thi Minh,García-Moreno, M. Isabel,Ortiz Mellet, Carmen,Nierengarten, Jean-Fran?ois,Compain, Philippe
, p. 7421 - 7430 (2016/09/09)
The synthesis of the first examples of multivalent C-glycosides based on C60-fullerene or β-cyclodextrin cores by way of Cu(i)-catalyzed azide-alkyne cycloadditions is reported. These compounds were designed as molecular probes to understand the mechanisms underlying the outstanding multivalent effects observed in glycosidase inhibition. The inhibition results obtained support a multivalent-binding model based on two scenarios both involving nonspecific interactions and varying by the presence or the absence of active site specific interactions. The magnitude of the multivalent effect obtained depends on the identity of the glycosidase involved and more specifically on the accessibility of its catalytic active site. Large inhibitory multivalent effects can be obtained when both glycosidase active sites and non-catalytic sites at the protein surface are involved in binding events. On the other hand, nonspecific interactions alone are not sufficient to achieve relative affinity enhancements exceeding a simple statistical effect (i.e., a relative inhibition potency not better than one on a valence-corrected basis).
