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

Shaw, Mukta; Kumar, Amit published the artcile< Additive-Free Gold(III)-Catalyzed Stereoselective Synthesis of 2-Deoxyglycosides Using Phenylpropiolate Glycosides as Donors>, Related Products of 4064-06-6, the main research area is deoxyglycoside stereoselective synthesis catalytic gold chloride; glycoside stereoselective glycosylation catalyzed gold disaccharide preparation phenylpropiolic acid; conformation transition state gold catalyzed stereoselective glycosylation disaccharide preparation; bifunctional donors; deoxy-phenylpropiolate; reusable and recyclable leaving group; stereoselective glycosylation.

Stereoselective synthesis of deoxyglycosides has been achieved from deoxy-phenylpropiolate glycosides (D-PPGs) using gold(III) salt as catalyst under external additive-free conditions. Under a simple catalytic system, D-PPGs reacted with a variety of sugar and non-sugar acceptors to produce major α-stereoselective O/N-deoxyglycosides in good to excellent yields and regenerate easily separable and reusable phenylpropiolic acid. Deoxy-PPGs containing armed and disarmed groups survived well under the optimized reaction conditions. In addition, the orthogonal nature of D-PPGs was showcased, and 1,1′-linked trehalose-type sugar was also synthesized.

Chemistry – An Asian Journal published new progress about Conformation. 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

Yang, Shao-Qian; Wang, Yi-Fan; Zhao, Wei-Cheng; Lin, Guo-Qiang; He, Zhi-Tao published the artcile< Stereodivergent Synthesis of Tertiary Fluoride-Tethered Allenes via Copper and Palladium Dual Catalysis>, Computed Properties of 4064-06-6, the main research area is fluoroester conjugated enyne copper palladium hydrocarbonation catalyst; allene stereoselective preparation gold cyclization; fluorinated hydrofuran stereoselective preparation.

Herein we describe a protocol for the unprecedented stereodivergent synthesis of tertiary fluoride-tethered allenes bearing a stereogenic center and stereogenic axis via Cu/Pd synergistic catalysis. A broad scope of conjugated enynes are coupled with various α-fluoroesters in high yields with high diastereoselectivities and generally >99% ee. In addition, the four stereoisomers of the allene products ensure precise access to the corresponding four stereoisomers of the fluorinated hydrofurans via a novel stereodivergent axial-to-central chirality transfer process.

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

Li, Xiaona; Li, Chenyu; Liu, Rongkun; Wang, Jiazhe; Wang, Zixuan; Chen, Yan; Yang, You published the artcile< Gold(I)-Catalyzed Glycosylation with Glycosyl Ynenoates as Donors>, 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 stereoselective glycosylation catalyst glycoside oligosaccharide preparation polysaccharide.

A simple and versatile glycosylation method with both armed and disarmed glycosyl ynenoates as donors is developed. Employing a gold(I) complex as catalyst with or without the assistance of TfOH, the scope of the present glycosylation protocol is very wide. The utility of the present ynenoate donors is demonstrated in the efficient synthesis of oligosaccharides via the latent-active strategy and the multiple orthogonal one-pot strategy. Finally, this approach enables the formal synthesis of the tetrasaccharide hapten of Streptococcus pneumoniae serotype 3 and the highly convergent synthesis of the 32mer polymannoside.

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, 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

Shaw, Mukta; Thakur, Rima; Kumar, Amit published the artcile< Gold(III)-Catalyzed Glycosylation using Phenylpropiolate Glycosides: Phenylpropiolic Acid, An Easily Separable and Reusable Leaving Group>, 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 disaccharide glycoside stereoselective glycosylation gold catalyst protecting group.

An efficient and operationally simple gold(III)-catalyzed glycosylation protocol was developed using newly synthesized bench top stable phenylpropiolate glycosyl (PPG) donors. Gold(III)-catalyzed activation of PPGs proceeds well with various carbohydrate and noncarbohydrate-based glycosyl acceptors and leads to their corresponding O/N-glycosides in good to excellent yields with regeneration of reusable and easily separable phenylpropiolic acid. Differentially protected PPGs reacted well under the optimized reaction conditions. In particular, good anomeric selectivity was observed with mannosyl and rhamnosyl PPG donors. A preliminary mechanistic study reveals that the presence of a triple bond adjacent to the ester group is essential for activation, and PPG-based donor shows higher reactivity than analogous acetate and benzoate donors.

Journal of Organic Chemistry 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, 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

Si, Xiaojia; Zhang, Lumin; Wu, Zuozuo; Rudolph, Matthias; Asiri, Abdullah M.; Hashmi, A. Stephen K. published the artcile< Visible Light-Induced α-C(sp3)-H Acetalization of Saturated Heterocycles Catalyzed by a Dimeric Gold Complex>, Related Products of 4064-06-6, the main research area is acetalization heterocycle gold catalyst visible light; cross coupling dehydrogenative ether tetrahydrothiophene pyrrolidine gold catalyst.

Saturated heterocyclic acetals are useful fragments in organic synthesis and other fields. Herein, C(sp3)-H dehydrogenative cross-couplings of ethers, tetrahydrothiophene, and N-Boc-pyrrolidine were achieved under visible light irradiation by using 4-iodoanisole and an in situ-formed gold complex. The broad functional group compatibility and substrate scope indicate that our strategy is a promising way to synthesize acetal analogs. The method was successfully applied in late-stage modifications of bioactive mols. Gram scale syntheses and mechanistic studies are also presented.

Organic Letters published new progress about Acetalization. 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

Trinderup, Helle H.; Andersen, Sofie M.; Heuckendorff, Mads; Jensen, Henrik H. published the artcile< How do Various Reaction Parameters Influence Anomeric Selectivity in Chemical Glycosylation with Thioglycosides and NIS/TfOH Activation?>, SDS of cas: 4064-06-6, the main research area is disaccharide preparation stereoselective glycosylation catalyst menthol thioglucopyranoside.

The reaction of glycosyl donor Ph 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside with NIS/TfOH(cat.) was systematically studied under various reaction conditions. Neither the mol. sieve pore size nor amount of NIS activator was found to have an effect on the α/β-ratio in the reaction with L-menthol as glycosyl acceptor. Increasing concentration and the amount of triflic acid catalyst, however was found to increase the β-selectivity in certain cases. Moreover, lowering temperature was found to have a strong effect on the glycosylation outcome.

European Journal of Organic Chemistry 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, SDS of cas: 4064-06-6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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.

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.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Sodano, Federica; Lazzarato, Loretta; Rolando, Barbara; Spyrakis, Francesca; De Caro, Carmen; Magliocca, Salvatore; Marabello, Domenica; Chegaev, Konstantin; Gazzano, Elena; Riganti, Chiara; Calignano, Antonio; Russo, Roberto; Rimoli, Maria Grazia published the artcile< Paracetamol-Galactose Conjugate: A Novel Prodrug for an Old Analgesic Drug>, 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 paracetamol galactose prodrug analgesic; X-ray diffraction; hepatotoxicity; hyperalgesia; metabolism; paracetamol; prodrug.

Paracetamol has been one of the most commonly used and prescribed analgesic drugs for more than a hundred years. Despite being generally well tolerated, it can result in high liver toxicity when administered in specific conditions, such as overdose, or in vulnerable individuals. We have synthesized and characterized a paracetamol galactosylated prodrug (PARgal) with the aim of improving both the pharmacodynamic and pharmacol. profile of paracetamol. PARgal shows a range of physicochem. properties, solubility, lipophilicity, and chem. stability at differing physiol. pH values and in human serum. PARgal could still be preclinically detected 2 h after administration, meaning that it displays reduced hepatic metabolism compared to paracetamol. In overdose conditions, PARgal has not shown any cytotoxic effect in in vitro analyses performed on human liver cells. Furthermore, when tested in an animal pain model, PARgal demonstrated a sustained analgesic effect up to the 12th hour after oral administration. These findings support the use of galactose as a suitable carrier in the development of prodrugs for analgesic treatment.

Molecular Pharmaceutics published new progress about Analgesia. 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

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.

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.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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