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methyl 4,6-O-benzylidene-3-O-benzyl-α-D-glucopyranoside is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

76419-48-2

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76419-48-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 76419-48-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,6,4,1 and 9 respectively; the second part has 2 digits, 4 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 76419-48:
(7*7)+(6*6)+(5*4)+(4*1)+(3*9)+(2*4)+(1*8)=152
152 % 10 = 2
So 76419-48-2 is a valid CAS Registry Number.

76419-48-2Relevant articles and documents

A Chiral Copper Catalyzed Site-Selective O-Alkylation of Carbohydrates

Ren, Bo,Wang, Jiaxi,Zhang, Mengyao,Chen, Yue,Zhao, Wei

supporting information, p. 665 - 670 (2021/12/02)

Highly regioselective alkylation of sugar hydroxyl groups has always been an important challenge in carbohydrate chemistry, especially for the selective alkylation of trans diols, there is no direct and efficient catalytic method so far. A chiral copper c

SnCl2-Catalyzed Acetalation/Selective Benzoylation Sequence for the Synthesis of Orthogonally Protected Glycosyl Acceptors

Dong, Hai,Feng, Guang-Jing,Guo, Yang-Fan,Liu, Chun-Yang,Lv, Jian

, (2022/04/03)

Based on SnCl2-catalyzed acetalation and selective benzoylation, a one-pot strategy to efficiently synthesize orthogonally protected glycosyl acceptors with 2-OH/3-OH was developed. Consequently, 2-OBz or 3-OBz 4,6-O-benzylidene galactosides and glucosides were efficiently prepared in moderate to high yields starting from free galactosides and glucosides, and were used as valuable glycosyl acceptors for the synthesis of blood group antigens O and B analogues in this study.

Carbohydrate-Derived Metal-Chelator-Triggered Lipids for Liposomal Drug Delivery

Holmstr?m, Thomas,Galsgaard Malle, Mette,Wu, Shunliang,Jensen, Knud J?rgen,Hatzakis, Nikos S.,Pedersen, Christian Marcus

supporting information, p. 6917 - 6922 (2021/02/26)

Liposomes are versatile three-dimensional, biomaterial-based frameworks that can spatially enclose a variety of organic and inorganic biomaterials for advanced targeted-delivery applications. Implementation of external-stimuli-controlled release of their cargo will significantly augment their wide application for liposomal drug delivery. This paper presents the synthesis of a carbohydrate-derived lipid, capable of changing its conformation depending on the presence of Zn2+: an active state in the presence of Zn2+ ions and back to an inactive state in the absence of Zn2+ or when exposed to Na2EDTA, a metal chelator with high affinity for Zn2+ ions. This is the first report of a lipid triggered by the presence of a metal chelator. Total internal reflection fluorescence microscopy and a single-liposome study showed that it indeed was possible for the lipid to be incorporated into the bilayer of stable liposomes that remained leakage-free for the fluorescent cargo of the liposomes. On addition of EDTA to the liposomes, their fluorescent cargo could be released as a result of the membrane-incorporated lipids undergoing a conformational change.

Regio/site-selective alkylation of substrates containing a: Cis -, 1,2- or 1,3-diol with ferric chloride and dipivaloylmethane as the catalytic system

Lv, Jian,Liu, Yu,Zhu, Jia-Jia,Zou, Dapeng,Dong, Hai

supporting information, p. 1139 - 1144 (2020/03/11)

In this study, we reported the regio/site-selective alkylation of substrates containing a cis-, 1,2- or 1,3-diol with FeCl3 as a key catalyst. A catalytic system consisting of FeCl3 (0.01-0.1 equiv.) and dipivaloylmethane (FeCl3/dipivaloylmethane = 1/2) was used to catalyze the alkylation in the presence of a base. The produced selectivities and isolated yields were similar to those obtained by methods using the same amount of FeL3 (L = acylacetone ligand) as the catalyst in most cases. The previously reported FeL3 catalysts for alkylation are not commercially available and have to be synthesized prior to use. In contrast, FeCl3 and dipivaloylmethane (Hdipm) are very common and inexpensive nontoxic reagents in the lab, thereby making the method much greener and easier to handle. Mechanism studies confirmed for the first time that FeCl3 initially reacts with two equivalents of Hdipm to form [Fe(dipm)3] in the presence of a base in acetonitrile, followed by the formation of a five or six-membered ring intermediate between [Fe(dipm)3] and two hydroxyl groups of the substrate. A subsequent reaction between the cyclic intermediate and the alkylating agent results in selective alkylation of the substrate.

Both d - And l -Glucose Polyphosphates Mimic d - myo-Inositol 1,4,5-Trisphosphate: New Synthetic Agonists and Partial Agonists at the Ins(1,4,5)P3Receptor

Shipton, Megan L.,Riley, Andrew M.,Rossi, Ana M.,Brearley, Charles A.,Taylor, Colin W.,Potter, Barry V. L.

, p. 5442 - 5457 (2020/07/21)

Chiral sugar derivatives are potential cyclitol surrogates of the Ca2+-mobilizing intracellular messenger d-myo-inositol 1,4,5-trisphosphate [Ins(1,4,5)P3]. Six novel polyphosphorylated analogues derived from both d- and l-glucose were synthesized. Binding to Ins(1,4,5)P3 receptors [Ins(1,4,5)P3R] and the ability to release Ca2+ from intracellular stores via type 1 Ins(1,4,5)P3Rs were investigated. β-d-Glucopyranosyl 1,3,4-tris-phosphate, with similar phosphate regiochemistry and stereochemistry to Ins(1,4,5)P3, and α-d-glucopyranosyl 1,3,4-tris-phosphate are full agonists, being equipotent and 23-fold less potent than Ins(1,4,5)P3, respectively, in Ca2+-release assays and similar to Ins(1,4,5)P3 and 15-fold weaker in binding assays. They can be viewed as truncated analogues of adenophostin A and refine understanding of structure-activity relationships for this Ins(1,4,5)P3R agonist. l-Glucose-derived ligands, methyl α-l-glucopyranoside 2,3,6-trisphosphate and methyl α-l-glucopyranoside 2,4,6-trisphosphate, are also active, while their corresponding d-enantiomers, methyl α-d-glucopyranoside 2,3,6-trisphosphate and methyl α-d-glucopyranoside 2,4,6-trisphosphate, are inactive. Interestingly, both l-glucose-derived ligands are partial agonists: they are among the least efficacious agonists of Ins(1,4,5)P3R yet identified, providing new leads for antagonist development.

Stereoselective Phenylselenoglycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides

Li, Zhongjun,Meng, Shuai,Yao, Wang,Zhong, Wenhe

, (2020/04/09)

A phenylselenoglycosylation reaction of glycal derivatives mediated by diphenyl diselenide and phenyliodine(III) bis(trifluoroacetate) under mild conditions is described. Stereoselective glycosylation has been achieved by installing fused carbonate on those glycals. 3,4-O-Carbonate galactals and 2,3-O-carbonate 2-hydroxyglucals are converted into corresponding glycosides in good yields with excellent β-selectivity, resulting in 2-phenylseleno-2-deoxy-β-galactosides and 2-phenylseleno-β-mannosides which are good precursors of 2-deoxy-β-galactosides and β-mannosides, respectively.

RETRACTED ARTICLE: Chemical synthesis and antigenic activity of a phosphatidylinositol mannoside epitope from: Mycobacterium tuberculosis

Zhao, Shi-Yuan,Li, Na,Luo, Wan-Yue,Zhang, Nan-Nan,Zhou, Rong-Ye,Li, Chen-Yu,Wang, Jin

, p. 14067 - 14070 (2020/11/21)

Phosphatidylinositol mannosides (PIMs) have been investigated as lipidic antigens for a new subunit tuberculosis vaccine. A non-natural diacylated phosphatidylinositol mannoside (Ac2PIM2) was designed and synthesized by mimicking the natural PIM6 processi

One-pot synthesis of orthogonally protected sugars through sequential base-promoted/acid-catalyzed steps: A solvent-free approach with self-generation of a catalytic species

Traboni, Serena,Bedini, Emiliano,Giordano, Maddalena,Iadonisi, Alfonso

supporting information, p. 1777 - 1780 (2019/06/07)

A varied set of solvent-free, one-pot synthetic sequences were developed to carry out the orthogonal protection of saccharide polyols. These sequences are composed of an initial regioselective benzylation, silylation or iodination (under mildly basic cond

KinITC—One Method Supports both Thermodynamic and Kinetic SARs as Exemplified on FimH Antagonists

Zihlmann, Pascal,Silbermann, Marleen,Sharpe, Timothy,Jiang, Xiaohua,Mühlethaler, Tobias,Jakob, Roman P.,Rabbani, Said,Sager, Christoph P.,Frei, Priska,Pang, Lijuan,Maier, Timm,Ernst, Beat

supporting information, p. 13049 - 13057 (2018/08/17)

Affinity data, such as dissociation constants (KD) or inhibitory concentrations (IC50), are widely used in drug discovery. However, these parameters describe an equilibrium state, which is often not established in vivo due to pharmacokinetic effects and they are therefore not necessarily sufficient for evaluating drug efficacy. More accurate indicators for pharmacological activity are the kinetics of binding processes, as they shed light on the rate of formation of protein–ligand complexes and their half-life. Nonetheless, although highly desirable for medicinal chemistry programs, studies on structure–kinetic relationships (SKR) are still rare. With the recently introduced analytical tool kinITC this situation may change, since not only thermodynamic but also kinetic information of the binding process can be deduced from isothermal titration calorimetry (ITC) experiments. Using kinITC, ITC data of 29 mannosides binding to the bacterial adhesin FimH were re-analyzed to make their binding kinetics accessible. To validate these kinetic data, surface plasmon resonance (SPR) experiments were conducted. The kinetic analysis by kinITC revealed that the nanomolar affinities of the FimH antagonists arise from both (i) an optimized interaction between protein and ligand in the bound state (reduced off-rate constant koff) and (ii) a stabilization of the transition state or a destabilization of the unbound state (increased on-rate constant kon). Based on congeneric ligand modifications and structural input from co-crystal structures, a strong relationship between the formed hydrogen-bond network and koff could be concluded, whereas electrostatic interactions and conformational restrictions upon binding were found to have mainly an impact on kon.

Synthesis and binding affinity analysis of α1-2- and α1-6-O/S-linked dimannosides for the elucidation of sulfur in glycosidic bonds using quartz crystal microbalance sensors

Norberg, Oscar,Wu, Bin,Thota, Niranjan,Ge, Jian-Tao,Fauquet, Germain,Saur, Ann-Kathrin,Aastrup, Teodor,Dong, Hai,Yan, Mingdi,Ramstr?m, Olof

supporting information, p. 35 - 42 (2017/10/25)

The role of sulfur in glycosidic bonds has been evaluated using quartz crystal microbalance methodology. Synthetic routes towards α1-2- and α1-6-linked dimannosides with S- or O-glycosidic bonds have been developed, and the recognition properties assessed in competition binding assays with the cognate lectin concanavalin A. Mannose-presenting QCM sensors were produced using photoinitiated, nitrene-mediated immobilization methods, and the subsequent binding study was performed in an automated flow-through instrumentation, and correlated with data from isothermal titration calorimetry. The recorded Kd-values corresponded well with reported binding affinities for the O-linked dimannosides with affinities for the α1-2-linked dimannosides in the lower micromolar range. The S-linked analogs showed slightly disparate effects, where the α1-6-linked analog showed weaker affinity than the O-linked dimannoside, as well as positive apparent cooperativity, whereas the α1-2-analog displayed very similar binding compared to the O-linked structure.

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