Category: 4064-06-6

Fleychuk, Roman; Vuytsyk, Lidiya; Kohut, Ananiy; Hevus, Orest published the artcile< Synthesis of epoxyperoxides and peroxide derivatives of α-D-galactopyranose based thereon>, Formula: C12H20O6, the main research area is galactopyranose peroxide preparation thermal stability.

New epoxide-containing peroxides were synthesized via the interaction between epichlorohydrin and ditertiary ω-hydroxyalkyl peroxides. The effect of reaction conditions on both the yield and composition of the reaction products was established. Through the reactions of either the synthesized epoxide-containing peroxides with 1,2;3,4-di-O-isopropylidene-α-D-galactopyranose or 6-O-glycidyl-1,2;3,4-di-O-isopropylidene-α-D-galactopyranose with the ω-hydroxyalkyl peroxides, new peroxide derivatives with ditertiary and primary-tertiary peroxide groups were synthesized successfully. The decomposition of the developed substances was studied by complex thermal anal. and the kinetic parameters of the thermolysis was determined

Chemistry & Chemical Technology published new progress about Activation energy. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Hu, Zhifei; Tang, Yu; Yu, Biao published the artcile< Glycosylation with 3,5-Dimethyl-4-(2'-phenylethynylphenyl)phenyl (EPP) Glycosides via a Dearomative Activation Mechanism>, SDS of cas: 4064-06-6, the main research area is glycosylation methylphenylethynylphenylphenyl steroid glycoside mechanism disaccharide.

A highly effective and versatile glycosylation method is developed, which uses 3,5-dimethyl-4-(2′-phenylethynylphenyl)phenyl (EPP) glycosides as donors and NIS/TMSOTf as promoter and proceeds via an unprecedented dearomative activation mechanism.

Journal of the American Chemical Society 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

Blaszczyk, Stephanie A.; Xiao, Guozhi; Wen, Peng; Hao, Hua; Wu, Jessica; Wang, Bo; Carattino, Francisco; Li, Ziyuan; Glazier, Daniel A.; McCarty, Bethany J.; Liu, Peng; Tang, Weiping published the artcile< S-Adamantyl Group Directed Site-Selective Acylation: Applications in Streamlined Assembly of Oligosaccharides>, Formula: C12H20O6, the main research area is regioselective acylation glycosylation glycoside; transition state steric DFT thioglycoside oligosaccharide thioglycosylation adamantane; acylation; carbohydrates; glycosylation; noncovalent interactions; synthetic methods.

The site-selective functionalization of carbohydrates is an active area of research. Reported here is the surprising observation that the sterically encumbered adamantyl group directed site-selective acylation at the C2 position of S-glycosides through dispersion interactions between the adamantyl C-H bonds and the π system of the cationic acylated catalyst, which may have broad implications in many other chem. reactions. Because of their stability, chem. orthogonality, and ease of activation for glycosylation, the site-selective acylation of S-glycosides streamlines oligosaccharide synthesis and will have wide applications in complex carbohydrate synthesis.

Angewandte Chemie, International Edition published new progress about Acylation. 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Formula: C12H20O6.

Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Dubey, Atul; Sangwan, Rekha; Mandal, Pintu Kumar published the artcile< N-benzoylglycine/thiourea cooperative catalyzed stereoselective O-glycosidation: Activation of O-glycosyl trichloroacetimidate 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 glycoside preparation benzoylglycine thiourea cooperative catalyzed stereoselective glycosidation; benzoylglycine thiourea cooperative catalyzed stereoselective glycosidation trichloroacetimidate donor activation.

A new practical utility for β-stereoselective glycosylation via activation of O-glycosyl trichloroacetimidate donors using N-benzoylglycine/thiourea cooperative catalysis has been demonstrated. This method represents the first instance where amino acid derived N-benzoylglycine is used as a catalyst for O-glycosylation under mild reaction conditions at ambient temperature NMR spectroscopy studies suggest that thiourea cocatalyst exhibit a cooperative behavior that has a strong effect on the reaction rate, yield, and the β-selectivity.

Catalysis Communications published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent). 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

Wang, Yulei; Huang, Zhidao; Huang, Zheng published the artcile< Catalyst as colour indicator for endpoint detection to enable selective alkyne trans-hydrogenation with ethanol>, Category: alcohols-buliding-blocks, the main research area is trans alkene stereoselective preparation; internal alkyne ethanol trans hydrogenation iridium catalyst.

An iridium complex catalyzed semi-hydrogenation of internal alkynes using ethanol as hydrogen donor to afford E-alkenes and Et acetate was reported. Importantly, issues of over-reduction and stereoselection was successfully addressed by using a color change effect due to shift of catalyst resting states, thereby precisely detecting the endpoint of the reaction. This catalytic system was applicable to a wide variety of internal alkynes bearing many auxiliary functional groups, and its utility for synthesis of biol. relevant mols. was also demonstrated.

Nature Catalysis published new progress about Alkenes Role: SPN (Synthetic Preparation), 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

Wu, Jicheng; Li, Xiaolei; Qi, Xiaotian; Duan, Xiyan; Cracraft, Weston L.; Guzei, Ilia A.; Liu, Peng; Tang, Weiping published the artcile< Site-Selective and Stereoselective O-Alkylation of Glycosides by Rh(II)-Catalyzed Carbenoid Insertion>, Application In Synthesis of 4064-06-6, the main research area is transition state crystal structure glycoside preparation disaccharide; crystal structure glycoside preparation stereoselective glycosylation catalyst disaccharide; rhodium catalyzed regioselective stereoselective glycosylation alkylation glycoside preparation DFT; regioselective stereoselective glycosylation protecting group alkylation glycoside carbenoid catalyzed.

Carbohydrates are synthetically challenging mols. with vital biol. roles in all living systems. Selective synthesis and functionalization of carbohydrates provide tremendous opportunities to improve our understanding on the biol. functions of this fundamentally important class of mols. However, selective functionalization of seemingly identical hydroxyl groups in carbohydrates remains a long-standing challenge in chem. synthesis. We herein describe a practical and predictable method for the site- and stereoselective alkylation of carbohydrate hydroxyl groups via Rh(II)-catalyzed insertion of metal carbenoid intermediates. This represents one of the mildest alkylation methods for the systematic modification of carbohydrates. D. functional theory (DFT) calculations suggest that the site-selectivity is determined in the Rh(II)-carbenoid insertion step, which prefers insertion into hydroxyl groups with an adjacent axial substituent. The subsequent intramol. enolate protonation determines the unexpected high stereoselectivity. The most prevalent trans-1,2-diols in various pyranoses can be systematically and predictably differentiated based on the model derived from DFT calculations We also demonstrated that the selective O-alkylation method could significantly improve the efficiency and stereoselectivity of glycosylation reactions. The alkyl groups introduced to carbohydrates by OH insertion reaction can serve as functional groups, protecting groups, and directing groups.

Journal of the American Chemical Society published new progress about Alkylation. 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

Geringer, Scott A.; Singh, Yashapal; Hoard, Daniel J.; Demchenko, Alexei V. published the artcile< A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis>, Synthetic Route of 4064-06-6, the main research area is cooperative silver catalyzed glycosidation benzoyl benzyl protected glycosyl chloride; activation; carbohydrates; glycosyl chlorides; glycosylation; silver oxide.

Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag2O.

Chemistry – A European Journal published new progress about Benzoyl group (protecting). 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

Geringer, Scott A.; Singh, Yashapal; Hoard, Daniel J.; Demchenko, Alexei V. published the artcile< A Highly Efficient Glycosidation of Glycosyl Chlorides by Using Cooperative Silver(I) Oxide-Triflic Acid Catalysis>, Synthetic Route of 4064-06-6, the main research area is cooperative silver catalyzed glycosidation benzoyl benzyl protected glycosyl chloride; activation; carbohydrates; glycosyl chlorides; glycosylation; silver oxide.

Following our discovery that silver(I) oxide-promoted glycosylation with glycosyl bromides can be greatly accelerated in the presence of catalytic TMSOTf or TfOH, we report herein a new discovery that glycosyl chlorides are even more effective glycosyl donors under these reaction conditions. The developed reaction conditions work well with a variety of glycosyl chlorides. Both benzoylated and benzylated chlorides have been successfully glycosidated, and these reaction conditions proved to be effective in coupling substrates containing nitrogen and sulfur atoms. Another convenient feature of this glycosylation is that the progress of the reaction can be monitored visually; its completion can be judged by the disappearance of the characteristic dark color of Ag2O.

Chemistry – A European Journal published new progress about Benzoyl group (protecting). 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

Wang, Jiazhe; Lou, Qixin; Rong, Jingjing; Yang, You published the artcile< Gold(I)-promoted α-selective sialylation of glycosyl ortho-hexynylbenzoates for the latent-active synthesis of oligosialic acids>, Synthetic Route of 4064-06-6, the main research area is sialoside capsular polysaccharide meningitidis; oligosialic acid coupling gold catalyst stereoselective sialylation hexynylbenzoate synthesis.

A gold(I)-promoted α-selective sialylation approach with 5-N,4-O-oxazolidinone-protected sialyl ortho-hexynylbenzoates as donors is described for the stereoselective synthesis of α-sialosides. Iterative couplings of the ‘active’ sialyl ortho-hexynylbenzoates and the ‘latent’ sialyl ortho-iodobenzoates provide a new approach for the ‘latent-active’ synthesis of α-(2→9)-linked oligosialic acids that are relevant to N. meningitidis sero-group C capsular polysaccharide.

Organic & Biomolecular Chemistry published new progress about Coupling reaction. 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

Hoang, Kevin M.; Lees, Nicholas R.; Herzon, Seth B. published the artcile< Programmable Synthesis of 2-Deoxyglycosides>, 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 deoxyglycoside synthesis programmable oligosaccharide stereoselective glycosylation.

Control of glycoside bond stereochem. is the central challenge in the synthesis of oligosaccharides. 2-Deoxyglycosides, which lack a C2 substituent to guide stereoselectivity, are among the most difficult classes of glycoside bond constructions. Here we present a method to synthesize 2-deoxysaccharides with specified glycoside bond stereochem. using a nucleophilic carbohydrate residue and the synthetic equivalent of an alc. electrophile. Because the configuration of the nucleophile can be precisely controlled, both α- and β-glycosides can be synthesized from the same starting material in nearly all cases examined Stereoselectivities in these reactions are often greater than 50:1 and yields typically exceed 70%. This strategy is amenable to the stereocontrolled syntheses of trisaccharide diastereomers, and a tetrasaccharide. This method may be extensible to other classes of carbohydrates.

Journal of the American Chemical Society 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