Category: 4064-06-6

Imperio, Daniela; Muz, Barbara; Azab, Abdel Kareem; Fallarini, Silvia; Lombardi, Grazia; Panza, Luigi published the artcile< A Short and Convenient Synthesis of closo-Dodecaborate Sugar Conjugates>, Application of C12H20O6, the main research area is boron neutron capture therapy dodecaborate sugar conjugate.

Dodecaborate anions represent a suitable boron source for boron neutron capture therapy (BNCT). Sugar derivatives of dodecaborate have been prepared through the ring-opening reaction of cyclic oxonium ions by alkoxide nucleophiles. According to this general approach, a convenient and short synthesis of three derivatives of dodecaborate-sugar conjugates is herein reported. Glucose, galactose and fructose have been chosen for their expected preferential uptake by tumor cells compared to healthy cells. The free hydroxyl group of isopropylidene protected sugars was exploited as nucleophile to open a dodecaborate cyclic oxonium salt, giving products containing a spacer between the sugar and the boron cluster. Deprotection of the sugar moiety in acidic conditions gave the desired compounds in excellent yield.

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Yu, Fei; Dickson, Jalen L.; Loka, Ravi S.; Xu, Hengfu; Schaugaard, Richard N.; Schlegel, H. Bernhard; Luo, Long; Nguyen, Hien M. published the artcile< Diastereoselective sp3 C-O Bond Formation via Visible Light-Induced, Copper-Catalyzed Cross-Couplings of Glycosyl Bromides with Aliphatic Alcohols>, Application of C12H20O6, the main research area is LED copper catalyzed diastereoselective coupling bromoglycoside aliphatic alc; C(sp3)–O bond; copper catalysis; cross-coupling; stereoselective; visible light.

Copper-catalyzed cross-coupling reactions have become one of the most powerful methods for generating carbon-heteroatom bonds, an important framework of many organic mols. However, copper-catalyzed C(sp3)-O cross-coupling of alkyl halides with alkyl alcs. remains elusive because of the sluggish nature of oxidative addition to copper. To address this challenge, we have developed a catalytic copper system, which overcomes the copper oxidative addition barrier with the aid of visible light and effectively facilitates the cross-couplings of glycosyl bromides with aliphatic alcs. to afford C(sp3)-O bonds with high levels of diastereoselectivity. Importantly, this catalytic system leads to a mild and efficient method for stereoselective construction of α-1,2-cis glycosides, which are of paramount importance, but challenging. In general, stereochem. outcomes in α-1,2-cis glycosidic C-O bond-forming processes are unpredictable and dependent on the steric and electronic nature of protecting groups bound to carbohydrate coupling partners. Currently, the most reliable approaches rely on the use of a chiral auxiliary or hydrogen-bond directing group at the C2- and C4-position of carbohydrate electrophiles to control α-1,2-cis selectivity. In our approach, earth-abundant copper not only acts as a photocatalyst and a bond-forming catalyst, but also enforces the stereocontrolled formation of anomeric C-O bonds. This cross-coupling protocol enables highly diastereoselective access to a wide variety of α-1,2-cis-glycosides and biol. relevant α-glycan oligosaccharides. Our work provides a foundation for developing new methods for the stereoselective construction of natural and unnatural anomeric carbon(sp3)-heteroatom bonds.

ACS Catalysis published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent) (glycoside). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application of C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhou, Siai; Zhong, Xuemei; Guo, Aoxin; Xiao, Qian; Ao, Jiaming; Zhu, Wanmeng; Cai, Hui; Ishiwata, Akihiro; Ito, Yukishige; Liu, Xue-Wei; Ding, Feiqing published the artcile< ZnI2-Directed Stereocontrolled α-Glucosylation>, Category: alcohols-buliding-blocks, the main research area is glycoside preparation disaccharide oligosaccharide stereoselective glycosylation serine; transition state Gibbs free energy electron density stereoselective glycosylation.

Here we report a glucosylation strategy mediated by ZnI2, a cheap and mild Lewis acid, for the highly stereoselective construction of 1,2-cis-O-glycosidic linkages using easily accessible and common 4,6-O-tethered glucosyl donors. The versatility and effectiveness of the α-glucosylation strategy were demonstrated successfully with various acceptors, including complex alcs. This approach demonstrates the feasibility of the modular synthesis of various α-glucans with both linear and branched backbone structures.

Organic Letters published new progress about Disaccharides 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, Category: alcohols-buliding-blocks.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Schaugaard, Richard N.; Nguyen, Hien M.; Schlegel, H. Bernhard published the artcile< Alkyl Radical-Free Cu(I) Photo-catalytic Cross-Coupling: A Theoretical Study of Anomerically Specific Photo-catalyzed Glycosylation of Pyranosyl Bromide>, 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 reductive elimination transition state free energy cyclic voltammetry glycosylation; thermodn solvation chromophore copper iodide xantphos DTMP phenanthroline catalyst; photochem catalyzed glycosylation pyranosyl bromide cross coupling disaccharide preparation.

Previously, we reported a visible light-activated Cu(I) photocatalyst capable of facilitating C-O bond formation of glycosyl bromides and aliphatic alcs. with a high degree of diastereoselectivity. This catalyst functions equally well in the presence of radical traps, suggesting an entirely inner sphere mechanism atypical for heteroleptic Cu photocatalysis. Further, exptl. estimates put the chromophore reducing power at -1.30 V vs Ag/AgCl. This is much more pos. than the ~-2.0 V vs Ag/AgCl onset observed for irreversible reduction of glycosyl bromides in our experiments Theor. investigations were undertaken to explain the function of the catalyst. Outer sphere electron transfer from a chromophore to substrate was discounted based on thermodn. and electron transfer barriers determined by Marcus theory and non-equilibrium solvation calculations Addition of a nucleophilic alc. and oxidation of the Cu(II) species to Cu(III) result in rapid reductive elimination forming products and resetting the catalytic cycle.

Inorganic Chemistry 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

Hedberg, Christinne; Jessen, Kamilla S.; Hansson, Rikke F.; Heuckendorff, Mads; Jensen, Henrik H. published the artcile< Palladium-Catalyzed C-S Bond Formation as a Tool for Latent-Active Glycosylation>, Electric Literature of 4064-06-6, the main research area is thioglycoside stereoselective glycosylation oligosaccharide preparation; palladium copper triflate catalyst stereoselective glycosylation cross coupling oligosaccharide.

A high-yielding palladium-catalyzed C-S cross-coupling is presented for utilization in carbohydrate chem. as a key transformation for attachment of a second chelating sulfur atom that allows the exploitation of a latent-active glycosylation strategy with Cu(OTf)2 as the promoter. The novel approach employs o-Br-benzyl thioglycosides as latent glycosyl donors and o-SMe-benzyl thioglycosides as the active counterparts.

Organic Letters published new progress about Coupling reaction. 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

Zu, Yujia; Cai, Chenglin; Sheng, Jingyuan; Cheng, Lili; Feng, Yingle; Zhang, Shengyong; Zhang, Qi; Chai, Yonghai published the artcile< n-Pentenyl-Type Glycosides for Catalytic Glycosylation and Their Application in Single-Catalyst One-Pot Oligosaccharide Assemblies>, Synthetic Route of 4064-06-6, the main research area is pentenyl glycoside catalytic stereoselective glycosylation oligosaccharide preparation.

We have developed a new type of n-pentenyl-type glycosides that can be activated by catalytic amounts of promoter, Hg(NTf2)2 or PPh3AuCl/AgNTf2, at room temperature The mild activation conditions and outstanding stability of common protection/deprotection manipulations enable the enynyl donors to have broad applications in constructing various glycosidic bonds. Furthermore, under the Hg(NTf2)2-catalyzed conditions, the sequential activation of different types of donors was achieved, based on which a gentio-tetrasaccharide was synthesized via the newly developed single-catalyst one-pot strategy.

Organic Letters 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, Synthetic Route of 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Park, Simon S.; Gervay-Hague, Jacquelyn published the artcile< Step-economy synthesis of β-steryl sialosides using a sialyl iodide donor>, Reference of 4064-06-6, the main research area is crystal structure conformation sialic acid preparation steroid glycoside; steryl sialoside synthesis sialyl iodide neuraminic acid glycosylation.

Steryl glycosides are prevalent in nature and have unique biol. activities dictated by sterol structure, sugar composition, and the stereochem. attachment of the aglycon. A single configurational switch can have profound biol. consequences meriting the systematic study of structure and function relationships. Steryl congeners of N-acetyl neuraminic acid (NANA) impact neurobiol. processes and may also mediate host/microbe interactions. In order to study these processes, a platform for the synthesis of β-steryl sialosides has been established. Promoter-free glycosidations using a novel α-linked sialyl iodide donor efficiently provide unique amphiphilic sialoglycoconjugates for examining bioactivities in various systems.

Journal of Antibiotics published new progress about Amphiphiles. 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

Aumala, Ville; Mollerup, Filip; Jurak, Edita; Blume, Fabian; Karppi, Johanna; Koistinen, Antti E.; Schuiten, Eva; Voss, Moritz; Bornscheuer, Uwe; Deska, Jan; Master, Emma R. published the artcile< Biocatalytic production of amino carbohydrates through oxidoreductase and transaminase cascades>, 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 amino carboxydrate production biocatalysis oxidoreductase transaminase enzyme cascade; amination; biocatalysis; carbohydrates; domino reactions; enzymes.

Plant-derived carbohydrates are an abundant renewable resource. Transformation of carbohydrates into new products, including amine-functionalized building blocks for biomaterials applications, can lower reliance on fossil resources. Herein, biocatalytic production routes to amino carbohydrates, including oligosaccharides, are demonstrated. In each case, two-step biocatalysis was performed to functionalize D-galactose-containing carbohydrates by employing the galactose oxidase from Fusarium graminearum or a pyranose dehydrogenase from Agaricus bisporus followed by the ω-transaminase from Chromobacterium violaceum (Cvi-ω-TA). Formation of 6-amino-6-deoxy-D-galactose, 2-amino-2-deoxy-D-galactose, and 2-amino-2-deoxy-6-aldo-D-galactose was confirmed by mass spectrometry. The activity of Cvi-ω-TA was highest towards 6-aldo-D-galactose, for which the highest yield of 6-amino-6-deoxy-D-galactose (67%) was achieved in reactions permitting simultaneous oxidation of D-galactose and transamination of the resulting 6-aldo-D-galactose.

ChemSusChem published new progress about Agaricus bisporus (pyranose dehydrogenase from). 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

Xu, Chunfa; Loh, Charles C. J. published the artcile< A Multistage Halogen Bond Catalyzed Strain-Release Glycosylation Unravels New Hedgehog Signaling Inhibitors>, Safety of ((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 glycosylation catalyst glycoside triazole preparation; click alkyne azide triazole cycloaddition catalyst preparation glycoside antitumor.

Halogen bonding (XB) has recently emerged as a promising noncovalent activation mode that can be employed in catalysis. However, methodologies utilizing XB remain rare, and the hydrogen-bonding (HB) catalysis congeners are more widespread in comparison. Herein, we demonstrate a remarkable case whereby employment of XB catalysis in strain-release glycosylation generates O,N-glycosides in excellent anomeric selectivity exceeding HB activation. Deeper investigation unraveled XB catalyst dependencies on multiple stages of the mechanism and a hitherto unknown XB-glycosyl acceptor activation. We present a proof of concept to interrogate sp3-rich glycosidic chem. space for novel biol. activity, by integrating XB-catalyzed construction of a glycosidic compound collection, and evaluating these analogs via cell-based phenotypic screens. We show that XB-catalyzed strain-release glycosylation defines a new class of glycosides that inhibit the hedgehog signaling pathway through a nonsmoothened mode of action, opening new opportunities to combat acquired cancer resistance.

Journal of the American Chemical Society published new progress about 1,3-Dipolar cycloaddition reaction. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Safety of ((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

Lei, Jin-Cai; Ruan, Yu-Xiong; Luo, Sheng; Yang, Jin-Song published the artcile< Stereodirecting Effect of C3-Ester Groups on the Glycosylation Stereochemistry of L-Rhamnopyranose Thioglycoside Donors: Stereoselective Synthesis of α- and β-L-Rhamnopyranosides>, Application In Synthesis of 4064-06-6, the main research area is rhamnopyranoside stereoselective synthesis ester group stereodirecting glycosylation effect.

The tuning effect of C3-ester groups on the glycosylation stereochem. of L-rhamnopyranose (L-Rha) Et thioglycoside donors is described. On one hand, the L-Rha thioglycoside donors carrying 3-O-arylcarbonyl or levulinoyl group undergo highly α-selective glycosylation to afford a wide variety of α-L-rhamnoside products in high chem. yields. On the other hand, the glycosylation of the 3-O-4-nitropicoloyl and 2-pyrazinecarbonyl group substituted L-Rha thioglycosides displays β-stereoselectivity. Only or predominant β anomeric products are obtained when these L-Rha donors couple with the primary or reactive secondary acceptors, while the β-selectivity may decrease significantly when these donors react with less reactive secondary alcs. The synthetic utility of the newly developed α- and β-directing L-Rha donors I and II has been demonstrated by the efficient synthesis of a structurally unique trisaccharide III, which is derived from the cell wall polysaccharide of Sphaerotilus natans.

European Journal of Organic Chemistry published new progress about Alkoxycarbonyl groups. 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