Tag: M.W=250-300

Zeng, Jing; Wang, Ruobin; Zhang, Shuxin; Fang, Jing; Liu, Shanshan; Sun, Guangfei; Xu, Bingbing; Xiao, Ying; Fu, Dengxian; Zhang, Wenqi; Hu, Yixin; Wan, Qian published the artcile< Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars>, Application In Synthesis of 4064-06-6, the main research area is trisaccharide synthesis synthon avidinorubicin; stereoselective glycosylation hydrogen bond amino sugar oxyphosphonium.

Challenges for stereoselective glycosylation of deoxy sugars are notorious in carbohydrate chem. We herein report a novel strategy for the construction of the less investigated β-glycosidic bonds of 3,5-trans-3-amino-2,3,6-trideoxy sugars (3,5-trans-3-ADSs), which constitute the core structure of several biol. important antibiotics. Current protocol leverages a C-3 axial sulfonamide group in 3,5-trans-3-ADSs as a hydrogen-bond (H-bond) donor and substoichiometric phosphine oxide as an exogenous nucleophilic reagent (exNu) to establish an intramol. H-bond between the former and the derived α-oxyphosphonium ion. This pivotal interaction stabilizes the α-face-covered intermediate to inhibit the formation of the more reactive β-intermediate, thereby yielding reversed β-selectivity, which is unconventional for an ex-Nu-mediated glycosylation system. A wide range of substrates was accommodated, and good to excellent β-selectivities were ensured by this H-bonding-assisted exNu effect. The robustness of the current strategy was further attested by the architectural modification of natural products and drugs containing 3,5-trans-3-ADSs, as well as the synthesis of a trisaccharide unit in avidinorubicin.

Journal of the American Chemical Society published new progress about Crystal structure. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application In Synthesis of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dong, Youxian; Yuma, Madina; Mei, Yuling; Jiang, Nan; Yang, Guofang; Wang, Zhongfu; Zhang, Jianbo published the artcile< Copper-Catalyzed Stereoselective Synthesis of 2-Deoxygalactosides>, Formula: C12H20O6, the main research area is copper catalyst stereoselective glycosylation deoxygalactoside deoxygalactoside oligosaccharide glycoside disaccharide.

An efficient glycosylation method to synthesize 2-deoxy-O-galactosides based on a Cu(II)-catalyzed reaction without addnl. ligand has been developed. The glycosylation was amenable to different protected glycal donors and a wide range of acceptors including alcs., amino acids, sugars, and phenol, and proceeds with excellent yield and high α-selectivity under mild conditions. The reaction proceeds readily on a gram scale, and its versatility is exemplified in the synthesis of oligosaccharides.

Synlett published new progress about Disaccharides Role: SPN (Synthetic Preparation), PREP (Preparation). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Mal′shakova, Marina V.; Velegzhaninov, Ilya O.; Rasova, Elena E.; Belykh, Dmitry V. published the artcile< Novel chlorophyll a derivatives with ester-linked galactose fragments for photodynamic therapy and fluorescence diagnostics of cancer>, Reference of 4064-06-6, the main research area is chlorophyll galactose fragment photodynamic therapy fluorescence diagnostis cancer.

In the present work, a number of chlorophyll a derivatives were synthesized with galactose fragments with an ester bond between macrocycle and carbohydrate fragments. It showed that synthesized compounds fluoresce intensely inside HeLa cells, which enable these compounds to be considered as potential diagnostic agents and indicates their ability to remain in the cell in an unassocd. photoactive state – a necessary condition for the realization of a photodynamic action. It was determined that while all conjugates had comparable photoinduced toxicities, the conjugate with phorbin macrocycle fragment had a much lower dark toxicity, which corresponds to the trends noted earlier. In terms of a therapeutic window, conjugate significantly exceeds similar derivatives of chlorin e6 and is the most promising for further research.

Journal of Porphyrins and Phthalocyanines published new progress about Antitumor agents. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Reference of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Drummond, Michael J.; Ford, Courtney L.; Gray, Danielle L.; Popescu, Codrina V.; Fout, Alison R. published the artcile< Radical rebound hydroxylation versus H-atom transfer in non-heme iron(III)-hydroxo complexes: Reactivity and structural differentiation>, Synthetic Route of 76-84-6, the main research area is nonheme iron oxoglutarate enzyme mechanism hydroxylation H transfer.

The characterization of high-valent iron centers in enzymes has been aided by synthetic model systems that mimic their reactivity or structural and spectral features. For example, the cleavage of dioxygen often produces an iron(IV)-oxo that has been characterized in a number of enzymic and synthetic systems. In non-heme 2-oxogluterate dependent (iron-2OG) enzymes, the ferryl species abstracts an H-atom from bound substrate to produce the proposed iron(III)-hydroxo and caged substrate radical. Most iron-2OG enzymes perform a radical rebound hydroxylation at the site of the H-atom abstraction (HAA); however, recent reports have shown that certain substrates can be desatd. through the loss of a second H atom at a site adjacent to a heteroatom (N or O) for most native desaturase substrates. One proposed mechanism for the removal of the second H-atom involves a polar-cleavage mechanism (electron transfer-proton transfer) by the iron(III)-hydroxo, as opposed to a second HAA. Herein we report the synthesis and characterization of a series of iron complexes with hydrogen bonding interactions between bound aquo or hydroxo ligands and the secondary coordination sphere in ferrous and ferric complexes. Interconversion among the iron species is accomplished by stepwise proton or electron addition or subtraction, as well as H-atom transfer (HAT). The calculated bond dissociation free energies (BDFEs) of two ferric hydroxo complexes, differentiated by their noncovalent interactions and reactivity, suggest that neither complex is capable of activating even weak C-H bonds, lending further support to the proposed mechanism for desaturation in iron-2OG desaturase enzymes. Addnl., the ferric hydroxo species are differentiated by their reactivity toward performing a radical rebound hydroxylation of triphenylmethylradical. Our findings should encourage further study of the desaturase systems that may contain unique H-bonding motifs proximal to the active site that help bias substrate desaturation over hydroxylation.

Journal of the American Chemical Society published new progress about Conformation. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Synthetic Route of 76-84-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kitowski, Annabel; Bernardes, Goncalo J. L. published the artcile< A Sweet Galactose Transfer: Metabolic Oligosaccharide Engineering as a Tool To Study Glycans in Plasmodium Infection>, SDS of cas: 4064-06-6, the main research area is GLUT1 galactose O glycosylation plasmodium infection malaria; GLUT1 transporters; bioorthogonal chemistry; carbohydrates; inverse electron-demand Diels-Alder; malaria.

The introduction of chem. reporter groups into glycan structures through metabolic oligosaccharide engineering followed by bio-orthogonal ligation is an important tool to study glycosylation. We show the incorporation of synthetic galactose derivatives that bear terminal alkene groups in hepatic cells, with and without infection by Plasmodium berghei parasites, the causative agent of malaria. Addnl., we demonstrated the contribution of GLUT1 to the transport of these galactose derivatives, and observed a consistent increase in the uptake of these compounds going from naive to P. berghei-infected cells. Finally, we used MOE to study the interplay between Plasmodium parasites and their mosquito hosts, to reveal a possible transfer of galactose building blocks from the latter to the former. This strategy has the potential to provide new insights into Plasmodium glycobiol. as well as for the identification and characterization of key glycan structures for further vaccine development.

ChemBioChem published new progress about Cell culture. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, SDS of cas: 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Kumar, Manoj; Reddy, Thurpu Raghavender; Gurawa, Aakanksha; Kashyap, Sudhir published the artcile< Copper(II)-catalyzed stereoselective 1,2-addition vs. Ferrier glycosylation of ""armed"" and ""disarmed"" glycal donors>, Formula: C12H20O6, the main research area is trisaccharide stereoselective addition copper catalyzed glycoconjugate glycal nucleoside; amino acid glycoside preparation stereoselective glycosylation Ferrier glycal alc.

Selective activation of “”armed’ and ”disarmed”” glycal donors enabling the stereo-controlled glycosylations by employing Cu(II)-catalyst as the promoter has been realized. The distinctive stereochem. outcome in the process is mainly influenced by the presence of diverse protecting groups on the donor and the solvent system employed. The protocol is compatible with a variety of aglycons including carbohydrates, amino acids, and natural products to access deoxy-glycosides and glycoconjugates with high α-anomeric selectivity. Notably, the synthetic practicality of the method is amply verified for the stereoselective assembling of trisaccharides comprising 2-deoxy components. Mechanistic studies involving deuterated experiments validate the syn-diastereoselective 1,2-addition of acceptors on the double bond of armed donors.

Organic & Biomolecular Chemistry published new progress about Addition reaction catalysts, stereoselective. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Doan, Son H.; Hussein, Mohanad A.; Nguyen, Thanh Vinh published the artcile< Tropylium-promoted Ritter reactions>, Application In Synthesis of 76-84-6, the main research area is amide preparation microwave continuous flow; alc nitrile Ritter reaction tropylium salt catalyst.

Herein, the development of a new method using salts of the tropylium ion to promote the Ritter reaction was reported. This method works well on a range of alcs., e.g., 1-phenylethanol and nitriles, e.g., acetonitrile, giving the corresponding products, e.g., N-(1-phenylethyl)acetamide in good to excellent yields. This reaction protocol is amenable to microwave and continuous flow reactors, offering an attractive opportunity for further applications in organic synthesis.

Chemical Communications (Cambridge, United Kingdom) published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Application In Synthesis of 76-84-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sun, Tao; Lv, Tian; Wu, Jianbing; Zhu, Mingchao; Fei, Yue; Zhu, Jie; Zhang, Yihua; Huang, Zhangjian published the artcile< General Strategy for Integrated Bioorthogonal Prodrugs: Pt(II)-Triggered Depropargylation Enables Controllable Drug Activation In Vivo>, Synthetic Route of 4064-06-6, the main research area is bioorthogonal prodrug decaging platinum triggered depropargylation controllable drug activation.

Bioorthogonal decaging reactions for controllable drug activation within complex biol. systems are highly desirable yet extremely challenging. Herein, we find a new class of Pt(II)-triggered bioorthogonal cleavage reactions in which Pt(II) but not Pt(IV) complexes effectively trigger the cleavage of O/N-propargyl in a variety of ranges of caged mols. under biocompatible conditions. Based on these findings, we propose a general strategy for integrated bioorthogonal prodrugs and accordingly design a prodrug 16 (I), in which a Pt(IV) moiety is covalently connected with an O2-propargyl diazeniumdiolate moiety. It is found that I can be specifically reduced by cytoplasmic reductants in human ovarian cancer cells to liberate cisplatin, which subsequently stimulates the cleavage of O2-propargyl to release large amounts of NO in situ, thus generating synergistic and potent tumor suppression activity in vivo. Therefore, Pt(II)-triggered depropargylation and the integration concept might provide a general strategy for broad applicability of bioorthogonal cleavage chem. in vivo.

Journal of Medicinal Chemistry published new progress about Antitumor agents. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Synthetic Route of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Chen, Jian; Hansen, Thomas; Zhang, Qing-Ju; Liu, De-Yong; Sun, Yao; Yan, Hao; Codee, Jeroen D. C.; Schmidt, Richard R.; Sun, Jian-Song published the artcile< 1-Picolinyl-5-azido Thiosialosides: Versatile Donors for the Stereoselective Construction of Sialyl Linkages>, HPLC of Formula: 4064-06-6, the main research area is glycan sialooligosaccharide preparation sialylation picolinyl azido protected thiosialoside; directing groups; glycan antennae; glycosylation; sialoside; stereoselective sialylation.

With the picolinyl (Pic) group as a C-1 located directing group and N3 as versatile precursor for C5-NH2, a novel 1-Pic-5-N3 thiosialyl donor was designed and synthesized, based on which a new sialylation protocol was established. In comparison to conventional sialylation methods, the new protocol exhibited obvious advantages, including excellent α-stereoselectivity in the absence of a solvent effect, broad substrate scope encompassing the challenging sialyl 8- and 9-hydroxy groups of sialic acid acceptors, flexibility in sialoside derivative synthesis, high temperature tolerance and easy scalability. In particular, the applicability to the synthesis of complex and bioactive N-glycan antennae when combined with the MPEP glycosylation protocol via the “”latent-active”” strategy has been shown. Mechanistically, the excellent α-stereoselectivity of the novel sialylation protocol could be attributed to the dramatic electron-withdrawing effect of the protonated Pic groups, which was supported by control reactions and DFT calculations

Angewandte Chemie, International Edition published new progress about Diastereoselective synthesis. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, HPLC of Formula: 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Oloo, Williamson N.; Szavuly, Miklos; Kaizer, Jozsef; Que, Lawrence Jr. published the artcile< Nonheme diiron oxygenase mimic that generates a diferric-peroxo intermediate capable of catalytic olefin epoxidation and alkane hydroxylation including cyclohexane>, Computed Properties of 76-84-6, the main research area is nonheme diiron oxygenase mimic intermediate olefin epoxidation alkane hydroxylation.

Herein are described substrate oxidations with H2O2 catalyzed by [FeII(IndH)(CH3CN)3](ClO4)2 [IndH = 1,3-bis(2′-pyridylimino)isoindoline], involving a spectroscopically characterized (μ-oxo)(μ-1,2-peroxo)diiron(III) intermediate (2) that is capable of olefin epoxidation and alkane hydroxylation including cyclohexane. Species 2 also converts ketones to lactones with a decay rate dependent on [ketone], suggesting direct nucleophilic attack of the substrate carbonyl group by the peroxo species. In contrast, peroxo decay is unaffected by the addition of olefins or alkanes, but the label from H218O is incorporated into the epoxide and alc. products, implicating a high-valent iron-oxo oxidant that derives from O-O bond cleavage of the peroxo intermediate. These results demonstrate an ambiphilic diferric-peroxo intermediate that mimics the range of oxidative reactivities associated with O2-activating nonheme diiron enzymes.

Inorganic Chemistry published new progress about Alkenes Role: BUU (Biological Use, Unclassified), SPN (Synthetic Preparation), BIOL (Biological Study), USES (Uses), PREP (Preparation). 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Computed Properties of 76-84-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts