Category: 4098-06-0

Palo-Nieto, Carlos; Sau, Abhijit; Galan, M. Carmen published the artcile< Gold(I)-Catalyzed Direct Stereoselective Synthesis of Deoxyglycosides from Glycals>, Safety of (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is deoxyglycoside stereoselective synthesis gold catalyzed hydrofunctionalization glycal enol ether; oligosaccharide stereoselective synthesis gold catalyzed hydrofunctionalization glycal enol ether; glycosyl amino acid stereoselective synthesis gold catalyzed hydrofunctionalization glycal; glycoconjugate stereoselective synthesis gold catalyzed hydrofunctionalization glycal enol ether.

Au(I) in combination with AgOTf enables the unprecedented direct and ä¼?stereoselective catalytic synthesis of deoxyglycosides from glycals. Mechanistic investigations suggest that the reaction proceeds via Au(I)-catalyzed hydrofunctionalization of the enol ether glycoside. The room temperature reaction is high yielding and amenable to a wide range of glycal donors and OH nucleophiles.

Journal of the American Chemical Society published new progress about Amino acids Role: SPN (Synthetic Preparation), PREP (Preparation) (glycosyl). 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

Thiem, Joachim; Laupichler, Lothar published the artcile< Ferrier glycosylation for synthesis of O- and S-glycopeptides>, Application In Synthesis of 4098-06-0, the main research area is glycopeptide diastereoselective synthesis; Ferrier glycosylation.

Ferrier glycosylation could be employed for the syntheses of a range of unsaturated O- as well as S-glycopeptides. Thus, featuring high yields and in many cases convincing diastereomeric excesses, an efficient protocol for formation of this class of compounds was established.

Journal of Carbohydrate Chemistry published new progress about Diastereoselective synthesis. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Application In Synthesis of 4098-06-0.

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

Malinowski, Maciej; Thanh, Van Tran; de Robichon, Morgane; Lubin-Germain, Nadege; Ferry, Angelique published the artcile< Mild Palladium-Catalyzed Cyanation of Unprotected 2-Iodoglycals in Aqueous Media as Versatile Tool to Access Diverse C2-Glyco-analogs>, Electric Literature of 4098-06-0, the main research area is palladium catalyzed cyanation iodoglycal glycal.

Access to unprotected 2-cyano-glycals via a mild palladium-catalyzed cyanation of protecting groups-free 2-iodoglycals in aqueous media has been developed. Diverse glycal substrates including disaccharide-type were successfully obtained in good to excellent yields. These unprotected 2-cyano-glycal scaffolds were successfully derivatized to different C2-glyco-analogs.

Advanced Synthesis & Catalysis published new progress about Cyanation. 4098-06-0 belongs to class esters-buliding-blocks, and the molecular formula is C12H16O7, Electric Literature of 4098-06-0.

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

Buttar, Simran; Caine, Julia; Gone, Evelyne; Harris, Renee; Gillman, Jennifer; Atienza, Roxanne; Gupta, Ritu; Sogi, Kimberly M.; Jain, Lauren; Abascal, Nadia C.; Levine, Yetta; Repka, Lindsay M.; Rojas, Christian M. published the artcile< Glycal Metallanitrenes for 2-Amino Sugar Synthesis: Amidoglycosylation of Gulal-, Allal-, Glucal-, and Galactal 3-Carbamates>, Quality Control of 4098-06-0, the main research area is allosamidin chitinase inhibitor aziridine oxocarbenium; aziridine oxocarbenium rhodium catalyzed oxidative cyclization glycal carbamate chitinase; protecting group galactal carbamate amidoglycosylation conformational electronic factor; amidoglycosylation sugar synthesi glycal metallanitrene carbamate antibiotic.

The rhodium(II)-catalyzed oxidative cyclization of glycal 3-carbamates with in situ incorporation of an alc. nucleophile at the anomeric position provides access to a range of 2-amino sugars having 1,2-trans-2,3-cis stereochem., a structural motif present in compounds of medicinal and biol. significance such as the streptothricin group of antibiotics and the Chitinase inhibitor allosamidin. All of the diastereomeric D-glycal 3-carbamates have been investigated, revealing significant differences in anomeric stereoselectivity depending on substrate stereochem. and protecting groups. In addition, some substrates were prone to forming C3-oxidized dihydropyranone byproducts under the reaction conditions. Allal- and gulal 3-carbamates provided uniformly high stereo- and chemoselectivity, while for glucal substrates, acyclic, electron-withdrawing protecting groups at the 4O and 6O positions were required. Galactal 3-carbamates have been the most challenging substrates; formation of their amidoglycosylation products is most effective with an electron-withdrawing 6O-Ts substituent and a sterically demanding 4O-TBS group. These results suggest a mechanism whereby conformational and electronic factors determine the partitioning of an intermediate acyl nitrenoid between alkene addition, leading to amidoglycosylation, and C3-H insertion, providing the dihydropyranone byproduct. Along the amidoglycosylation pathway, high anomeric selectivity results when a glycosyl aziridine intermediate is favored over an aziridine-opened oxocarbenium donor.

Journal of Organic Chemistry published new progress about Conformation. 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

Jozsef, Janos; Juhasz, Laszlo; Somsak, Laszlo published the artcile< Thio-click reaction of 2-deoxy-exo-glycals towards new glycomimetics: stereoselective synthesis of C-2-deoxy-D-glycopyranosyl compounds>, COA of Formula: C12H16O7, the main research area is deoxyglycal Bamford Stevens deoxyglycopyranosylmethyl sulfide disaccharide; configuration deoxyglycopyranosyl cyanide anhydroaldose tosylhydrazone reduction tosylhydrazine.

A series of 2-deoxy-glycopyranosyl cyanides with D-arabino, D-lyxo, D-erythro, and D-threo configurations was synthesized from the corresponding glycals via 2-deoxy-glycopyranosyl acetates. The cyanides were transformed to anhydro-aldose tosyl-hydrazones by reduction with NaH2PO2/Ra-Ni in the presence of tosylhydrazine. The tosyl-hydrazones furnished 2-deoxy-exo-glycals under modified Bamford-Stevens conditions. Photo-initiated thiol-ene additions of these exo-glycals resulted in the corresponding C-(2-deoxy-D-glycopyranosyl)methyl sulfides in medium to good yields with exclusive regio- and stereoselectivities in most cases. Several disaccharide mimics with a C-S moiety in place of the glycosidic oxygen were also obtained.

New Journal of Chemistry published new progress about Aldoses 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, COA of Formula: C12H16O7.

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

Ghouilem, Juba; Tran, Christine; Grimblat, Nicolas; Retailleau, Pascal; Alami, Mouad; Gandon, Vincent; Messaoudi, Samir published the artcile< Diastereoselective Pd-Catalyzed Anomeric C(sp3)-H Activation: Synthesis of α-(Hetero)aryl C-Glycosides>, Computed Properties of 4098-06-0, the main research area is palladium catalyst stereoselective glycosylation heteroaryl aminoglycoside preparation; aryl aminoglycoside preparation crystal structure arylation stereoselective glycosylation heteroaryl.

Anomeric C-H bond activation is an unsolved long-standing synthetic challenge. Herein, we report a diastereoselective Pd-catalyzed anomeric C(sp3)-H activation methodol. that allows the synthesis of elusive C-(hetero)aryl glycosides with an exclusive α-selectivity.

ACS Catalysis 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, Computed Properties of 4098-06-0.

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

Meng, Shuai; Zhong, Wenhe; Yao, Wang; Li, Zhongjun published the artcile< Stereoselective Phenylseleno-glycosylation of Glycals Bearing a Fused Carbonate Moiety toward the Synthesis of 2-Deoxy-β-galactosides and β-Mannosides>, Product Details of C12H16O7, the main research area is selenide phenyliodine fluoroacetate phenylseleno glycosylation glycoside preparation; stereoselective glycosylation glycal fused carbonate synthesis deoxygalactoside mannoside glycoside.

A phenylseleno-glycosylation reaction of glycal derivatives mediated by di-Ph 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, resp.

Organic Letters published new progress about Glycals 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, Product Details of C12H16O7.

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

Saidhareddy, Puli; Ajay, Sama; Shaw, Arun K. published the artcile< Iodosobenzene diacetate-Iodine and IBX-Iodine: Reagent systems for the synthesis of diastereomerically enriched 2-deoxy-2-iodoglycosyl acetates and 2-deoxy-2-iodoglycosyl ortho-iodobenzoates from protected glycals>, Application In Synthesis of 4098-06-0, the main research area is hexose enolone preparation glycal stereoselective iodination glycoside disaccharide glycosylation; disaccharide preparation iodosobenzene acetate iodine stereoselective iodination protecting group.

Two efficient, metal free reagent systems, PhI(OAc)2-I2 (method A) and IBX-I2 (method B), for stereoselective synthesis of trans-2-deoxy-2-iodoglycosylacetates and O-iodobenzoates resp. from differently protected glycals have been developed. They are compatible with a variety of protecting groups and various functional groups at 2C-position. Hexose-3,2-enolone I is obtained directly from 2-acetoxy glycal II by method A. An application to modified method B has been shown by synthesis of a diastereomerically pure α-glycosyl ortho-hexynylbenzoate, a glycosyl donor from 3,4,6-tri-O-acetyl-D-glucal in two steps that has been further utilized in the synthesis of glycosides, e.g. III.

Tetrahedron published new progress about Disaccharides 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, Application In Synthesis of 4098-06-0.

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

Thakur, Kratima; Khare, Naveen K. published the artcile< Copper mediated A3-coupling reaction for the preparation of enantioselective deoxy sugar based chiral propargylamine using bifunctional ligand L-proline>, Recommanded Product: (2R,3R,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate, the main research area is glycoside propargylamine proline copper catalyst coupling preparation aldehyde; copper catalyst coupling preparation enantioselective deoxy sugar propargylamine proline; A(3)-coupling reaction; C–H bond activation; Enantioselectivity; Propargylamines; l-proline.

An efficient three component coupling of aromatic aldehyde, deoxy sugar based alkyne (α-2-deoxy propargyl glycoside) and heterocyclic amine have been refluxed to synthesize stereoselective chiral propargylamine with good to excellent yield using only CuI catalyst along with bifunctional ligand L-proline. This method has proved to be applicable in wide range of substrates and found highly enantioselective with respect to earlier reported methods. In addition, L-proline was found as a chiral source which demonstrated that it could be developed as a highly enantioselective method for the construction of deoxy sugar based chiral propargylamine. The ligand L-proline was used for the first time in enantioselective A3-coupling reaction of α-2-deoxy propargyl glycosides involving substituted aromatic aldehyde and heterocyclic amines. Herein, we have synthesized 15 novel compounds based on A3-coupling reaction and structures of all the enantioselective compounds were characterized by TLC and NMR spectroscopy.

Carbohydrate Research published new progress about Aryl aldehydes Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Urbanczyk, Malgorzata; Jewginski, Michal; Krzciuk-Gula, Joanna; Gora, Jerzy; Latajka, Rafal; Sewald, Norbert published the artcile< Synthesis and conformational preferences of short analogs of antifreeze glycopeptides (AFGP)>, Electric Literature of 4098-06-0, the main research area is antifreeze glycopeptide analog synthesis conformation hydrogen bond cluster NMR; threonine glycosylation azido galactosyl chloride reduction; solid phase peptide synthesis acetylation antifreeze activity; NMR; PP II; antifreeze glycopeptides; conformational preferences; solid phase synthesis.

Antifreeze glycoproteins are a class of biol. agents which enable living at temperatures below the f.p. of the body fluids. Antifreeze glycopeptides usually consist of repeating tripeptide unit (-Ala-Ala-Thr*-), glycosylated at the threonine side chain. However, on the microscopic level, the mechanism of action of these compounds remains unclear. As previous research has shown, antifreeze activity of antifreeze glycopeptides strongly relies on the overall conformation of the mol. as well an on the stereochem. of amino acid residues. The desired monoglycosylated analogs with acetylated amino termini and the carboxy termini in form of N-methylamide have been synthesized. Conformational NMR (NMR) studies of the designed analogs have shown a strong influence of the stereochem. of amino acid residues on the peptide chain stability, which could be connected to the antifreeze activity of these compounds A better understanding of the mechanism of action of antifreeze glycopeptides would allow applying these materials, e.g., in food industry and biomedicine.

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

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