Category: 4064-06-06 00:00:00

Zhou, Xin; Ding, Han; Chen, Pengwei; Liu, Li; Sun, Qikai; Wang, Xianyang; Wang, Peng; Lv, Zhihua; Li, Ming published the artcile< Radical Dehydroxymethylative Fluorination of Carbohydrates and Divergent Transformations of the Resulting Reverse Glycosyl Fluorides>, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is antidiabetic crystal mol structure human SGLT2 SGLT1 conformation; cyclic oligosaccharide disaccharide glycoside preparation radical dehydroxymethylative fluorination; C−F bond activation; alkoxyl radicals; carbohydrates; fluorination; radical reactions.

A mild and convenient method for the synthesis of reverse glycosyl fluorides (RGFs) has been developed that is based on the silver-promoted radical dehydroxymethylative fluorination of carbohydrates. A salient feature of the reaction is that furanoid and pyranoid carbohydrates furnish structurally diverse RGFs bearing a wide variety of functional groups in good to excellent yields. Intramol. hydrogen atom transfer experiments revealed that the reaction involves an under-exploited radical fluorination that proceeds via β-fragmentation of sugar-derived primary alkoxyl radicals. Structurally divergent RGFs were obtained by catalytic C-F bond activation, and our method thus offers a concise and efficient strategy for the synthesis of reverse glycosides by late-stage diversification of RGFs. The potential of this method is showcased by the preparation and diversification of sotagliflozin, leading to the discovery of a promising SGLT2 inhibitor candidate.

Angewandte Chemie, International Edition published new progress about Antidiabetic agents. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Seo, Kyeongdeok; Rhee, Young Ho published the artcile< Ruthenium-Catalyzed Regioselective Olefin Migration of Dihydropyran Acetals: A De Novo Strategy toward β-2,6-Dideoxypyranoglycosides>, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol, the main research area is ring closure metathesis catalyst; stereoselective glycosylation catalyst oligosaccharide preparation hydroxylation; regioselective olefin migration dihydropyran acetal ruthenium catalyzed deoxypyranoglycoside oligosaccharide; disaccharide trisaccharide oligosaccharide preparation deoxypyranoglycoside ruthenium catalyzed olefin migration.

Here, we report a de novo synthetic strategy toward β-2,6-dideoxypyranoglycosides. The key event is the ruthenium-catalyzed regioselective olefin migration of dihydropyran allylic acetals to homoallylic acetals. In combination with other metal-catalyzed reactions, this new protocol led to the synthesis of β-2,6-dideoxypyranoglycosides in a highly efficient manner. Using this sequential metal catalysis, various mono-, di-, and trisaccharide forms of β-2,6-dideoxypyranoglycosides were prepared

Organic Letters published new progress about Catalysis. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Recommanded Product: ((3aR,5R,5aS,8aS,8bR)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-5-yl)methanol.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Shadrick, Melanie; Singh, Yashapal; Demchenko, Alexei V. published the artcile< Stereocontrolled α-Galactosylation under Cooperative Catalysis>, Related Products of 4064-06-6, the main research area is disaccharide preparation stereoselective galactosylation catalyzed; stereoselective galactosylation catalyzed protecting group glycosyl halide glycoside preparation.

A recent discovery of a cooperative catalysis comprising a silver salt and an acid led a dramatic improvement in the way glycosyl halides are glycosylated. Excellent yields have been achieved, but the stereoselectivity achieved with 2-O-benzylated donors was poor. Reported herein is our first attempt to refine the stereoselectivity of the cooperatively catalyzed galactosylation reaction. Careful optimization of the reaction conditions along with studying effects of the remote protecting groups led to excellent stereocontrol of α-galactosylation of a variety of glycosyl acceptors with differentially protected glycosyl donors.

Journal of Organic Chemistry published new progress about Catalysis. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Related Products of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Singh, Yashapal; Demchenko, Alexei V. published the artcile< Defining the Scope of the Acid-Catalyzed Glycosidation of Glycosyl Bromides>, Electric Literature of 4064-06-6, the main research area is acid catalyzed Koenigs Knorr glycosidation glycosyl bromide alc acceptor; catalysis; glycosylation; mechanism; oligosaccharides; stereoselectivity.

Following the recent discovery that traditional silver(I) oxide-promoted glycosidations of glycosyl bromides (Koenigs-Knorr reaction) can be greatly accelerated in the presence of catalytic TMSOTf, reported herein is a dedicated study of all major aspects of this reaction. A thorough investigation of numerous silver salts and careful refinement of the reaction conditions led to an improved mechanistic understanding. This, in turn, led to a significant reduction in the amount of silver salt required for these glycosylations. The progress of this reaction can be monitored by naked eye, and the completion of the reaction can be judged by the disappearance of characteristic dark color of Ag2O. Further evidence on higher reactivity of benzoylated α-bromides in comparison to that of their benzylated counterparts has been acquired.

Chemistry – A European Journal published new progress about Glycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (bromides). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Electric Literature of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Li, Qiuhan; Levi, Samuel M.; Jacobsen, Eric N. published the artcile< Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea>, Reference of 4064-06-6, the main research area is selective thiourea catalyzed mannosylation rhamnosylation acetonide protective group effect.

We report highly β-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alc. nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.

Journal of the American Chemical Society published new progress about Amino acids Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (glycosides). 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

Zheng, Zhitong; Zhang, Liming published the artcile< Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor>, Category: alcohols-buliding-blocks, the main research area is glucoside stereoselective synthesis gold catalyzed glycosylation ethynylphenyl thioglucoside donor; 1,2-cis glycosidic bond; Glucosylation; Gold catalysis; S(N)2 pathway; o-ethynylphenyl β-D-1-thioglucoside.

A gold-catalyzed glucosylation method using an o-ethynylphenyl β-D-1-thioglucoside as donor is described. The reaction proceeds in a mostly SN2 pathway. A series of α-D-glucosides are obtained in good yields and with up to 19:1 α-selectivity.

Carbohydrate Research published new progress about Glucosylation catalysts (stereoselective). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhang, Cheng; Li, Hongli; Pei, Chao; Qiu, Lihua; Hu, Wenhao; Bao, Xiaoguang; Xu, Xinfang published the artcile< Selective Vinylogous Reactivity of Carbene Intermediate in Gold-Catalyzed Alkyne Carbocyclization: Synthesis of Indenols>, Category: alcohols-buliding-blocks, the main research area is diazo alkyne nucleophile gold catalyst regioselective regioselective carbocyclization DFT; indenol preparation.

A gold-catalyzed carbocyclization of alkynes with a pendant diazo group that is completed by reaction with a protic nucleophile for the synthesis of indenol derivatives with a tertiary center is described. Mechanistic studies and DFT calculations indicate that the transformation is initiated by a gold-promoted 5-endo-dig carbocyclization to form the key intermediate vinyl gold carbene, which is intercepted by an unprecedented vinylogous addition and followed by external protic nucleophile-assisted protodeauration. Furthermore, in this catalytic alkyne transformation, various nucleophiles, including water, com. available 1°, 2°, and 3° alcs., menthol, D-galactose, cholesterol, steroid, etc., all perform well under these mild conditions to produce the corresponding indenol derivatives in high yields with structural diversity.

ACS Catalysis published new progress about Alkynes Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation) (diazo esters). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Komura, Naoko; Kato, Keiichi; Udagawa, Taro; Asano, Sachi; Tanaka, Hide-Nori; Imamura, Akihiro; Ishida, Hideharu; Kiso, Makoto; Ando, Hiromune published the artcile< Constrained sialic acid donors enable selective synthesis of α-glycosides>, COA of Formula: C12H20O6, the main research area is sialic acid synthesis glycoside stereoselective glycosylation sialooligosaccharide.

Sialic acid is a sugar residue present in many biol. significant glycans of mammals, commonly as a terminal α-glycoside. The chem. structure of sialic acid, which features an anomeric center with carboxyl and methylene substituents, poses a challenge for synthesis of the α-glycoside, thus impeding biol. and therapeutic studies on sialic acid-containing glycans. We present a robust method for the selective α-glycosylation of sialic acid using macro-bicyclized sialic acid donors as synthetic equivalent of structurally constrained oxocarbenium ions to impart stereoselectivity. We demonstrate the power of our method by showcasing broad substrate scope and applicability in the preparation of diverse sialic acid-containing architectures.

Science (Washington, DC, United States) published new progress about Glycosides Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, COA of Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dang, Huiping; Tian, Youliang; Cheng, Quan; Teng, Changchang; Xie, Kai; Yan, Lifeng published the artcile< Galactose conjugated boron dipyrromethene and hydrogen bonding promoted J-aggregates for efficiently targeted NIR-II fluorescence assistant photothermal therapy>, Computed Properties of 4064-06-6, the main research area is galactose conjugated boron dipyrromethene hydrogen bond fluorecence tumor imaging; 4, 4-difluoro-4-bora-3a, 4a-diazas-indacene (BODIPY); Galactose conjugated; Imaging-guided; NIR-II fluorescence; Photothermal therapy.

It is essential to develop novel multifunctional and easily synthesized stable NIR-II fluorescent probes to guide photothermal therapy for tumors. Here, we propose a new strategy to construct boron dipyrromethene (BODIPY) J-aggregates by intermol. hydrogen bonding (H-bond) and π-π stacking interactions to achieve fluorescence emission in the second near-IR window (NIR-II, 1000-1700 nm). A novel meso-benzamide galactose hexanoate-BODIPY (Gal-OH-BDP) amphiphilic small mol. dye was synthesized and it formed nanoparticles spontaneously in aqueous solution with a maximum emission wavelength near 1060 nm, which works as a smart nanomedicine for targeting NIR-II imaging-guided photothermal therapy (PTT) of hepatocellular carcinoma. Galactose not only provided hydrogen bonds to regulate the aggregation pattern of the mols. but also effectively targeted hepatocellular carcinoma cells and promoted the formation of well-dispersed nanoparticles of dye mols. due to their hydrophilicity. Moreover, due to high photothermal conversion efficiency (PCE = 55%), Gal-OH-BDP NPs achieve galactose-targeted NIR-II imaging and PTT, which is important for the precise diagnosis and treatment of tumors (Scheme 1). In the present research work, H-bond was introduced for the first time into BODIPY for building J-aggregates to achieve the NIR-II fluorescence.

Journal of Colloid and Interface Science published new progress about Cytotoxicity. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Computed Properties of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zheng, Lifang; Luo, Yan; Chen, Kui; Zhang, Zexin; Chen, Gaojian published the artcile< Highly Branched Gradient Glycopolymer: Enzyme-Assisted Synthesis and Enhanced Bacteria-Binding Ability>, COA of Formula: C12H20O6, the main research area is highly branched glycopolymer preparation.

A one-pot strategy was applied to synchronize enzymic monomer transformation with reversible addition fragmentation chain transfer (RAFT) polymerization for the synthesis of glycopolymers with highly branched gradient architectures. Also, the linear analogs, block glycopolymers, and gradient glycopolymers were also synthesized for comparison. The binding ability of glycopolymers toward bacteria was then studied by optical d. (OD) test, confocal laser scanning microscopy (CLSM), and quartz crystal microbalance with dissipation (QCM-D). The results show that the highly branched gradient glycopolymers have the most remarkable bacteria-binding ability compared with the two linear analogs, gradient glycopolymers, and block glycopolymers. The highly branched glycopolymers were further used as inhibitors in the anti-infection test, demonstrating a significant inhibitory effect on preventing bacteria from infecting the cells.

Biomacromolecules published new progress about RAFT polymerization. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, COA of Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts