M.W=250-300 Archives - Page 55 of 59 - Alcohols-buliding-blocks

Mei, Yuling’s team published research in Journal of Carbohydrate Chemistry in 2020 | 4064-06-6

Journal of Carbohydrate Chemistry published new progress about C-Glycosides Role: SPN (Synthetic Preparation), PREP (Preparation). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Mei, Yuling; Dong, Youxian; Li, Juan; Zhang, Bo; Sun, Guosheng; Zhou, Jiafen; Si, Wenshuai; Han, Yiwen; Wu, Zhenliang; Zhang, Jianbo published the artcile< FeCl3/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-O-Benzyl-D-glucal>, Formula: C12H20O6, the main research area is stereoselective glycosylation glycal alc preparation glycoside rearrangement Ferrier.

FeCl3/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-D-glucal, which is a relatively un-reactive substrate for this type of reaction. The method was applicable to a wide range of alcs., especially phenols. A series of 2,3-unsaturated-O-glucosides were prepared efficiently (47-92%) by this method under mild conditions.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Zhou, Xin’s team published research in Angewandte Chemie, International Edition in 2020-03-09 | 4064-06-6

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.

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.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ngai, Courtney’s team published research in Angewandte Chemie, International Edition in 2022-03-07 | 76-84-6

Angewandte Chemie, International Edition published new progress about Directed assembly. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Recommanded Product: Triphenylmethanol.

Ngai, Courtney; Wu, Hoi-Ting; da Camara, Bryce; Williams, Christopher G.; Mueller, Leonard J.; Julian, Ryan R.; Hooley, Richard J. published the artcile< Moderated Basicity of Endohedral Amine Groups in an Octa-Cationic Self-Assembled Cage>, Recommanded Product: Triphenylmethanol, the main research area is preparation moderated basicity endohedral octa cationic self assembled cage; mol structure moderated basicity endohedral octa cationic self assembled; Coordination Chemistry; Enzyme Models; Molecular Recognition; Self-Assembly; Supramolecular Chemistry.

A self-assembled FeII4L6 cage was synthesized with 12 internal amines in the cavity. The cage forms as the dodeca-ammonium salt, despite the cage carrying an overall 8+ charge at the metal centers, extracting protons from displaced water in the reaction. Despite this, the basicity of the internal amines is lower than their counterparts in free solution The 12 amines have a sliding scale of basicity, with a ≈ 6 pKa unit difference between the first and last protons to be removed. This moderation of side-chain basicity in an active site is a hallmark of enzymic catalysis.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Liu, Miao’s team published research in Angewandte Chemie, International Edition in 2020 | 4064-06-6

Angewandte Chemie, International Edition published new progress about Glycals Role: RCT (Reactant), RACT (Reactant or Reagent). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application In Synthesis of 4064-06-6.

Liu, Miao; Liu, Kai-Meng; Xiong, De-Cai; Zhang, Hanyu; Li, Tian; Li, Bohan; Qin, Xianjin; Bai, Jinhe; Ye, Xin-Shan published the artcile< Stereoselective Electro-2-deoxyglycosylation from Glycals>, Application In Synthesis of 4064-06-6, the main research area is nucleoside stereoselective glycosylation glycal synthesis electrochem; stereoselective glycosylation glycal electrochem deoxyglycosylation podophyllotoxin trisaccharide synthesis; 2-deoxyglycosides; carbohydrates; electrocatalysis; glycals; glycosylation.

We report a novel and highly stereoselective electro-2-deoxyglycosylation from glycals. This method features excellent stereoselectivity, scope, and functional-group tolerance. This process can also be applied to the modification of a wide range of natural products and drugs. Furthermore, a scalable synthesis of glycosylated podophyllotoxin and a one-pot trisaccharide synthesis through iterative electro-glycosylation were achieved.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Seo, Kyeongdeok’s team published research in Organic Letters in 2020-03-20 | 4064-06-6

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.

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

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Shadrick, Melanie’s team published research in Journal of Organic Chemistry in 2020-12-18 | 4064-06-6

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.

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

Akhrem, Irena S’s team published research in ChemistrySelect in 2020-06-29 | 76-84-6

ChemistrySelect published new progress about Aromatic alcohols Role: SPN (Synthetic Preparation), PREP (Preparation). 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Quality Control of 76-84-6.

Akhrem, Irena S.; Avetisyan, Dzhul’etta V.; Afanas’eva, Lyudmila V.; Artyushin, Oleg I. published the artcile< Simple and Efficient ""One-Pot"" Synthesis of Diphenylaryl (Heteroaryl) Methanols from Benzene>, Quality Control of 76-84-6, the main research area is diphenyl aryl methanol preparation.

A simple and efficient one-pot method for the synthesis of diphenyl(aryl)methanols I [Ar = Ph, 4-FC6H4, 2-thienyl, etc.] from benzene was developed using the known reaction of benzene with CCl4·AlCl3. This approach appeared fruitful when the reaction was performed uring CCl4 as a solvent. This method allowed the selective synthesis of Ph2CCl2 in good yield.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Pandey, Akanksha M’s team published research in Journal of Organic Chemistry in 2022-08-05 | 76-84-6

Journal of Organic Chemistry published new progress about Aromatic alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Recommanded Product: Triphenylmethanol.

Pandey, Akanksha M.; Mondal, Shankhajit; Gnanaprakasam, Boopathy published the artcile< Continuous Flow Direct Azidation of Alcohols and Peroxides for the Synthesis of Quinoxalinones, Benzooxazinone and Triazole Derivatives>, Recommanded Product: Triphenylmethanol, the main research area is aryl azide preparation; aromatic alc azidation continuous flow; azide benzoxazinone preparation; peroxide indole ring expansion azidation continuous flow; quinoxalinone azide preparation; indole azide ring expansion skeletal rearrangement continuous flow.

The continuous flow direct azidation of various alcs. by using TMSN3 as an azide transfer reagent in the presence of Amberlyst-15 as a recyclable catalyst was reported. Numerous 3-hydroxy-2-oxindoles e.g., diphenylmethanol effectively undergo azide transfer reaction to afford azide functionalized quaternary stereocenter e.g., [azido(phenyl)methyl]benzene under continuous flow module. Interestingly, peroxyoxindole undergoes sequential skeletal rearrangement to generate carbocation and followed by nucleophilic azidation to afford a library of substituted-2-azido-2H-benzo[b][1,4]oxazin-3(4H)-one derivatives I (R = 4-methoxyphenyl, Me, Bn, etc.; R1 = H, Me, Bn) under continuous flow. Furthermore, a continuous-flow Cu-catalyzed Click reaction afforded triazole functionalized derivatives II (R2 = Me, Ph). Next, reduction of azide in the presence of PPh3 results the amine derivatives in good yield. The continuous-flow application was extended further for the thermolytic skeletal rearrangement of 3-azide-2-oxindole for the synthesis of biol. important quinoxalin-2(1H)-ones III (R3 = Me, Bn, 4-MeC6H4, etc.) under reagentless condition. Furthermore, this continuous-flow direct azidation reaction is scaled up to 6.144 g of azides with TON = 9.24 under safer condition.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Aman, Hasil’s team published research in ChemistrySelect in 2020-11-23 | 76-84-6

ChemistrySelect published new progress about Aralkyl alcohols Role: RCT (Reactant), SPN (Synthetic Preparation), RACT (Reactant or Reagent), PREP (Preparation). 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Recommanded Product: Triphenylmethanol.

Aman, Hasil; Chen, Yuan-Ching; Tu, Jing-Wen; Chang, Chia-Chi; Chuang, Gary Jing published the artcile< Catalyst/Additive Free Oxidation of Benzyl Bromides to Benzaldehydes>, Recommanded Product: Triphenylmethanol, the main research area is benzyl bromide Kornblum oxidation; benzaldehyde preparation green chem.

An effective approach for the synthesis of aryl aldehydes from the corresponding benzyl bromides was accomplished. Without need of addnl. additives or stoichiometric oxidants, this environmental friendly and milder version of Kornblum oxidation simply utilized the irradiation of visible light in DMSO under O2, and was compatible with the substrate with different functional groups.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Ueno, Masaharu’s team published research in European Journal of Organic Chemistry in 2019 | 76-84-6

European Journal of Organic Chemistry published new progress about Green chemistry. 76-84-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C19H16O, Computed Properties of 76-84-6.

Ueno, Masaharu; Kusaka, Ryo; Ohmura, Satoshi D.; Miyoshi, Norikazu published the artcile< Environmentally Benign Ritter Reaction Using Bismuth Salts as a Catalyst>, Computed Properties of 76-84-6, the main research area is Ritter bismuth salt catalyst green.

The authors developed an environmentally benign Ritter reaction of alcs. with nitriles using a com. available bismuth salt as a less harmful catalyst. The detailed reaction profiles revealed that consumption of the ether byproduct as the reaction proceeded was the key for optimizing this reaction, and the yield of the target amide was improved by adding a small amount of water. This finding clearly reveals the significance of using a bismuth salt as the catalyst, as it is not deactivated in the presence of water. This catalyst system has a broad substrate scope, and even with 1 mol-% of the catalyst, the reaction progresses smoothly. It is also possible to react stoichiometric amounts of nitriles and alcs., thus reducing the amount of organic solvent required for the reaction. Furthermore, as the inexpensive bismuth catalyst can be easily removed using aqueous hydrochloric acid, a purification process that only required washing and drying without any organic solvents was successfully established.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts