Category: 4098-06-0

Bi, Jingjing; Tan, Qiang; Wu, Hao; Liu, Qingfeng; Zhang, Guisheng published the artcile< Rhodium-Catalyzed Denitrogenative Trans-annulation of N-Sulfonyl-1,2,3-triazoles with Glycals Giving Pyrroline-Fused N-Glycosides>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is crystal structure aminoglycoside stereoselective cyclization sulfonyl triazole glycal; stereoselective cyclization aminoglycoside preparation rhodium catalyzed sulfonyl triazole glycal; aminoglycoside preparation rhodium catalyzed annulation sulfonyl triazole pyrroline glycoside.

Described here is a selective synthesis of 2,3-dihydropyrrole-fused N-glycosides through rhodium-catalyzed denitrogenation trans-annulation of N-sulfonyl-1,2,3-triazoles with glycals. A series of pyrroline-fused N-glycosides are afforded in moderate to excellent yields with exclusive regioselectivity and stereoselectivity. Functional application of such a resultant product by oxidative addition and epoxidation is also explored. Notably, the treatment of a pyrroline-fused N-glycoside (3a) with TMSOTf efficiently leads to an interesting unexpected C-nucleoside I via a TMSOTf-inducing ring opening/acetyl migration/ring closing reaction sequence.

Organic Letters published new progress about Aminoglycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Ram, Ram N.; Kumar, Neeraj; Kumar Gupta, Dharmendra published the artcile< Substrate-Controlled Diastereoselective Synthesis of Sugar-Based Chlorinated Perhydrofuro[2,3-b]pyrans via Copper(I)-Catalyzed Radical Cyclization>, Synthetic Route of 4098-06-0, the main research area is Ferrier rearrangement chloroethanol acetal glucal cyclization glycoside disaccharide preparation; crystal structure disaccharide stereoselective cyclization copper catalyzed hydrofuropyran chlorinated.

The work describes the first copper(I) chloride/2,2′-bipyridine-catalyzed atom transfer radical cyclization (ATRC) of unsaturated carbohydrate-derived chloroacetals to generate chlorinated perhydrofuro[2,3-b]pyrans via an effective diastereoselective route. Various glycals (glucal, galactal and lactal) underwent the Ferrier rearrangement with 2,2,2-trichloroethanols to give acetal precursors stereoselectively, R-selective with galactal in contrast to S-selective with glucal. The radical cyclization of the Ferrier products occurred smoothly to afford cis-fused bicyclic products with the transfer of the chlorine atom at the non-anomeric carbon in the cyclized radical intermediate predominantly from the equatorial direction. The carbohydrate templates controlled the stereochem. of both Ferrier rearrangement and ATRC steps. The stereo-structures of the products were also supported by single crystal X-ray diffraction crystallog. The products possess biol. important structural segments such as a glycosidic linkage, a fused bicyclic acetal unit and a chlorosugar unit which are potential sources for biol. studies and further synthetic elaborations.

Advanced Synthesis & Catalysis published new progress about Bicyclic compounds Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Synthetic Route of 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Shang, Wenbin; Zhu, Chunyu; Peng, Fengyuan; Pan, Zhiqiang; Ding, Yuzhen; Xia, Chengfeng published the artcile< Nitrogen-Centered Radical-Mediated Cascade Amidoglycosylation of Glycals>, Quality Control of 4098-06-0, the main research area is aminodeoxyglycoside aminoglycoside disaccharide TEMPO catalyst cascade stereoselective amidoglycosylation.

A nitrogen-centered radical-mediated strategy for preparing 1,2-trans-2-amino-2-deoxyglycosides in one step was established. The cascade amidoglycosylation was initiated by a benzenesulfonimide radical generated from NFSI under the catalytic reduction of TEMPO. The benzenesulfonimide radical was electrophilically added to the glycals, and then the resulting glycosidic radical was converted to oxocarbenium upon oxidation by TEMPO+, which enabled the following anomeric specific glycosylation.

Organic Letters published new progress about Aminoglycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Quality Control of 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Perlikova, Pavla; Kvasnica, Miroslav; Urban, Milan; Hajduch, Marian; Sarek, Jan published the artcile< 2-Deoxyglycoside Conjugates of Lupane Triterpenoids with High Cytotoxic Activity-Synthesis, Activity, and Pharmacokinetic Profile>, SDS of cas: 4098-06-0, the main research area is preparation deoxyglycoside conjugate lupane triterpenoid cancer structure pharmacokinetics.

A set of 41 glycosidic conjugates of pentacyclic triterpenes was synthesized in order to improve the solubility of highly cytotoxic parent compounds Their in vitro cytotoxic activity was evaluated in 25 cancer cell lines and 2 noncancer fibroblasts. Fifteen compounds had high cytotoxicity on the T-lymphoblastic leukemia cell line CCRF-CEM and 6 of them were active in multiple cell lines of various histogenic origin and not toxic in fibroblasts. Compound 11a had IC50 of 0.64μM in CCRF-CEM cells, 0.60μM in K-562 cells, and 0.37μM in PC-3 cells; compound 12a had IC50 of 0.64μM in CCRF-CEM cells and 0.71μM in SW620 cells; compound 17b had IC50 of 0.86μM in HCT116 cells and 0.92μM in PC-3 cells. Compounds 11b and 12b were slightly less active than the previously mentioned derivatives; however, their solubility was significantly better, and therefore they were selected for the in vivo evaluation of the pharmacokinetic profile in mice. In both compounds, the maximum concentration in plasma was achieved very rapidly-the highest level in plasma was found 1 h after administration (22.2, resp., 6.4μM). For compound 12b, the resorption was followed with fast elimination, and 12 h after administration, the compound was not detected in plasma. In contrast, compound 11b was eliminated more slowly; it was still present in plasma after 12 h, but its concentration dropped below the detection limit after 24 h. The elimination half-time determined for compound 11b was 2.4 h and for compound 12b just about 1.4 h. These values are reasonable for further drug development.

Bioconjugate Chemistry published new progress about Antitumor agents. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, SDS of cas: 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Addanki, Rupa Bai; Halder, Suvendu; Kancharla, Pavan K. published the artcile< TfO-···H-O-H Interaction-Assisted Generation of a Silicon Cation from Allylsilanes: Access to Phenylallyl Ferrier Glycosides from Glycals>, Category: esters-buliding-blocks, the main research area is organocatalyst diastereoselective Ferrier glycosylation glycal allylsilane hydrogen bond; crystal structure diastereoselective phenylallyl Ferrier glycoside allylsilane silicon cation.

We demonstrate here that the strained and bulky protonated 2,4,6-tri-tert-butylpyridine (TTBPy) triflate salt serves as a mild and efficient organocatalyst for the diastereoselective C-Ferrier glycosylation of various glycals. The criticality of the role of 1/2 H2O mol. trapped in the catalyst has been disclosed. The mechanism of action involves unique anionic triflate and H2O hydrogen bond interactions assisting the activation of allylsilanes that provides unprecedented access to diastereoselective phenylallyl Ferrier glycosides.

Organic Letters published new progress about Crystal structure. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Category: esters-buliding-blocks.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Lazzara, Nicholas C.; Rosano, Robert J.; Vagadia, Purav P.; Giovine, Matthew T.; Bezpalko, Mark W.; Piro, Nicholas A.; Kassel, Wm. Scott; Boyko, Walter J.; Zubris, Deanna L.; Schrader, Kevin K.; Wedge, David E.; Duke, Stephen O.; Giuliano, Robert M. published the artcile< Synthesis and Biological Evaluation of 6-[(1R)-1-Hydroxyethyl]-2,4a(R),6(S),8a(R)-tetrahydropyrano-[3,2-b]-pyran-2-one and Structural Analogues of the Putative Structure of Diplopyrone>, Reference of 4098-06-0, the main research area is hydroxyethyl tetrahydropyrano pyranone analog preparation fungicide antibiotic phytotoxic catfish.

The phytotoxin diplopyrone is considered to be the main phytotoxin in a fungus that is responsible for cork oak decline. A carbohydrate-based synthesis of the enantiomer of the structure proposed for diplopyrone has been developed from a com. available derivative of D-galactose. Key steps in the synthesis are a highly stereoselective pyranose chain-extension based on methyltitanium, preparation of a vinyl glycoside via Isobe C-alkynylation-rearrangement/reduction, and RCM-based pyranopyran construction. Crystallog. and NMR anal. confirms an earlier report that the structure originally proposed for diplopyrone may require revision. Structural analogs were prepared for biol. evaluation, the most promising being a pyranopyran nitrile synthesized from tri-O-acetyl-D-galactal by Ferrier cyanoglycosidation, Wittig chain extension, and lactonization. Biol. assays revealed potent antibacterial activity for the nitrile analog against common bacterial pathogens Edwardsiella ictaluri and Flavobacterium columnare that cause enteric septicemia (ESC) and columnaris disease, resp., in catfish. The IC50 value of 0.002 against E. ictaluri indicates approx. 100 times greater potency than the antibiotic florfenicol used com. for this disease. Phytotoxic activity for all three target compounds against duckweed was also observed The antibiotic and phytotoxic activities of the new pyranopyrans synthesized in this study demonstrate the potential of such compounds as antibiotics and herbicides.

Journal of Organic Chemistry published new progress about Alkynylation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Reference of 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Keith, D. Jamin; Townsend, Steven D. published the artcile< Total Synthesis of the Congested, Bisphosphorylated Morganella morganii Zwitterionic Trisaccharide Repeating Unit>, Safety of (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is zwitterionic polysaccharide immune response phosphoglycerol phosphocholine oligosaccharide; oligosaccharide Morganella Morganii trisaccharide repeating unit Zwitterionic phosphorylated glycosylation.

Zwitterionic polysaccharides (ZPS) activate T-cell-dependent immune responses by major histocompatibility complex class II presentation. Herein, we report the first synthesis of a Morganella morganii ZPS repeating unit as an enabling tool in the synthesis of novel ZPS materials. The repeating unit incorporates a 1,2-cis-α-glycosidic bond; the problematic 1,2-trans-galactosidic bond, Gal-β(1→3)-GalNAc; and phosphoglycerol and phosphocholine residues which have not been previously observed together as functional groups on the same oligosaccharide. The successful third generation approach leverages a first in class glycosylation of a phosphoglycerol functionalized acceptor. To install the phosphocholine unit, a highly effective phosphocholine donor was synthesized.

Journal of the American Chemical Society published new progress about Glycosylation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Safety of (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Saima, Yasmin; Khamarui, Saikat published the artcile< MnVI-NP-Catalyzed Generation of Nitrile Oxides: Easy Access to Isoxazolines and Isoxazoles via Stereoselective 1,3-Dipolar Cycloaddition Reactions>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is aldoxime alkene manganese catalyst chemoselective regioselective diastereoselective dipolar cycloaddition; isoxazole preparation; alkyne aldoxime manganese catalyst chemoselective regioselective diastereoselective dipolar cycloaddition; isoxazoline preparation.

The versatility and effectiveness of Mn(VI)-nanoparticles as a catalyst is examined for the generation of nitrile oxides from aldoximes and subsequent 1,3-dipolar cycloaddition reactions. This synthetic protocol features fast reaction convergence under benign reaction conditions, operational simplicity, and the use of inexpensive precursors; it avoids the use of acids or bases. The strategy offers excellent chemo-, regio-, and diastereoselectivity in the 1,3-dipolar cycloaddition reaction of in situ-generated nitrile oxides with alkenes and alkynes.

SynOpen published new progress about 1,3-Dipolar cycloaddition catalysts. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Thakur, Kratima; Khare, Naveen K. published the artcile< Synthesis of glycoconjugate mimics by 'click chemistry'>, HPLC of Formula: 4098-06-0, the main research area is click alkyne azide triazole cycloaddition catalyst preparation; triazole glycoconjugate preparation stereoselective library mol structure; 1,3-Dipolar cycloaddition; Click reaction; CuI; Glycoconjugates; Stereoselectivity.

Stereo-defined 2-deoxy propargyl glycosides can be used for the synthesis of corresponding 1,4-disubstituted sugar derived triazoles by using only CuI and stereo-defined sugar azide derivatives The click chem. which involves copper (I) catalyzed alkyne-azide 1,3-dipolar cycloaddition, was used to prepare a library of glycoconjugates mimics. Different sugar propargyl-2-deoxy-O-α-D-glycopyranoside derivatives and β-glycopyranosyl azide derivatives were coupled using catalyst CuI to yield triazole glycoconjugates. The catalyst CuI (2.5 equivalent) in CH3CN was found to be most efficient for the synthesis of 1,4-disubstituted triazole scaffolds affording up to 94% of optimized yield and with retention of the anomeric configuration of the starting glycosides. The key feature of this methodol. is the absence of sodium L-ascorbate/ascorbic acid which is most active substrate of current research with strong potential for click reactions. In this article, the library of novel stereoselective deoxy sugar derived triazole glycoconjugates have been synthesized and structures were determined by the 1H, 13C & 2D NMR spectroscopy.

Carbohydrate Research published new progress about 1,3-Dipolar cycloaddition reaction. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, HPLC of Formula: 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Thakur, Kratima; Khare, Naveen K. published the artcile< Synthesis of glycoconjugate mimics by 'click chemistry'>, HPLC of Formula: 4098-06-0, the main research area is click alkyne azide triazole cycloaddition catalyst preparation; triazole glycoconjugate preparation stereoselective library mol structure; 1,3-Dipolar cycloaddition; Click reaction; CuI; Glycoconjugates; Stereoselectivity.

Stereo-defined 2-deoxy propargyl glycosides can be used for the synthesis of corresponding 1,4-disubstituted sugar derived triazoles by using only CuI and stereo-defined sugar azide derivatives The click chem. which involves copper (I) catalyzed alkyne-azide 1,3-dipolar cycloaddition, was used to prepare a library of glycoconjugates mimics. Different sugar propargyl-2-deoxy-O-α-D-glycopyranoside derivatives and β-glycopyranosyl azide derivatives were coupled using catalyst CuI to yield triazole glycoconjugates. The catalyst CuI (2.5 equivalent) in CH3CN was found to be most efficient for the synthesis of 1,4-disubstituted triazole scaffolds affording up to 94% of optimized yield and with retention of the anomeric configuration of the starting glycosides. The key feature of this methodol. is the absence of sodium L-ascorbate/ascorbic acid which is most active substrate of current research with strong potential for click reactions. In this article, the library of novel stereoselective deoxy sugar derived triazole glycoconjugates have been synthesized and structures were determined by the 1H, 13C & 2D NMR spectroscopy.

Carbohydrate Research published new progress about 1,3-Dipolar cycloaddition reaction. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, HPLC of Formula: 4098-06-0.

Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics