69351-19-5

Upstream product

• 25018-67-1 1,2;4,5-di-O-isopropylidene-β-D-(-)-fructopyranose 
• 57-48-7 D-Fructose 
• 77-76-9 2,2-dimethoxy-propane 
• 7660-25-5 D-fructose 
• 15080-25-8 C₁₂H₂₀O₆ 
• 6347-01-9 fructopyranose 
• 20880-92-6 2,3;4,5-di-O-isopropylidene-β-D-fructopyranose 

Downstream Products

• 108680-92-8 1,2:4,5-di-O-isopropylidene-3-C-phenyl-β-D-fructopyranose 
• 18422-54-3 1,2;4,5-di-O-isopropylidene-β-D-fructopyranose 
• 187236-00-6 C₂₃H₃₀O₆ 
• 439828-63-4 (5S,8R,9R)-2,2-dimethyl-10-oxo-1,3,6-trioxaspiro[4,5]decane-8,9-diyl diacetate 
• 532394-78-8 3-O-benzoyl-3-C-cyano-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose 
• 532394-80-2 1,2:4,5-di-O-isopropylidene-3-C-(5-phenyl-1,2,4-oxadiazol-3-yl)-β-D-psicopyranose 
• 532394-79-9 3-O-benzoyl-3-C-(N-hydroxycarbamimidoyl)-1,2:4,5-di-O-isopropylidene-β-D-psicopyranose 
• 187236-13-1 (5S,8R,9R,10R)-9-Methoxy-2,2-dimethyl-10-(5-phenyl-pentyl)-1,3,6-trioxa-spiro[4.5]decane-8,10-diol 

Relevant academic research and scientific papers

Studies on asymmetric total synthesis of (?)-β-hydrastineviaa chiral epoxide ring-opening cascade cyclization strategy

Herein, facile and enantioselective approaches to synthesize the core phthalide tetrahydroisoquinoline scaffold of (?)-β-hydrastineviaboth a CF3COOH-catalyzed (86% ee) and KHMDS-catalyzed (78% ee) epoxide ring-opening/transesterification cascade cyclization from chiral epoxide under very mild conditions are described. The key elements include a highly enantioselective epoxidation using the Shi ketone catalyst and an intramolecular CF3COOH-catalyzed cascade cyclization in one pot, and a late-stage C-3′ epimerization under MeOK/MeOH conditions as the key steps to achieve the first total synthesis of (?)-β-hydrastine (up to 81% ee).

IMPROVED SYNTHESIS OF AN EPOXIDATION-CATALYST

The present invention relates to an improved process to produce a specific and very efficient epoxidation-catalyst (1,2:4,5-Di-O-isopropylidene-β-D-erythro-2,3-hexodiulo-2,6-pyranose).

Safe and Scalable Aerobic Oxidation by 2-Azaadamantan-2-ol (AZADOL)/NOx Catalysis: Large-Scale Preparation of Shi's Catalyst

A method for safe and scalable aerobic alcohol oxidation using 2-azaadamantan-2-ol (AZADOL), an azaadamantane-type hydroxylamine catalyst, with a NOx cocatalyst in a conventional batch reactor has been developed. The use of 2 mol % AZADOL and 10 mol % NaNO2 was determined to promote aerobic alcohol oxidation quantitatively within a reasonable time (8 h). Safety is ensured by controlling the reaction temperature below the flash point of the acetic acid solvent. The robustness of the developed method is demonstrated by the 500 g scale oxidation of diacetone fructose into Shi's catalyst for asymmetric epoxidation.

Synthesis method of fructose-derived chiral ketone catalyst

The invention provides a synthesis method of a fructose-derived chiral ketone catalyst. The method comprises the following steps: (1) by using D-fructose and acetone as a raw material, carrying out ketonization reaction at 10-45 DEG C by using concentrated sulfuric acid as a catalyst to obtain a first intermediate; (2) dissolving the first intermediate in an organic solvent, adding molecular sieve powder, and carrying out oxidation at 50-80 DEG C by using PCC as an oxidant, thereby obtaining a second intermediate; (3) carrying out hydrolysis on the second intermediate at 10-45 DEG C under the actions of acetic acid, water and zinc chloride, thereby obtaining a third intermediate; after the hydrolysis finishes, adding acetic anhydride, and carrying out esterification reaction to obtain a fructose-derived chiral ketone hydrate; and (4) eliminating water molecules in the fructose-derived chiral ketone hydrate by using a polar organic solvent, thereby obtaining the fructose-derived chiral ketone. The method has the advantages of simple technique, low raw material cost and mild reaction conditions, is convenient for separation and purification, can be used for quickly and efficiently synthesizing the fructose-derived chiral ketone catalyst, and is more suitable for industrial production.

An alkoxyamine compound, alkoxy alcohol oxidation catalyst and method of using the alcohol oxidation

PROBLEM TO BE SOLVED: To provide a novel alkoxyamine compound which can be easily manufactured and applied suitably as an alcohol oxidation catalyst capable of exerting sufficiently high catalytic activity in oxidation of primary and secondary alcohols.SOLUTION: There is provided an alkoxyamine compound with a homoadamantane skeleton represented by the general formula (1) in the figure. [In the formula (1), Rand Rare each independently any one selected from the group consisting of a hydrogen atom and alkyl groups that may be substituted.

Stable TEMPO and ABNO Catalyst Solutions for User-Friendly (bpy)Cu/Nitroxyl-Catalyzed Aerobic Alcohol Oxidation

Two solutions, one consisting of bpy/TEMPO/NMI and the other bpy/ABNO/NMI (bpy =2,2′-bipyridyl; TEMPO = 2,2,6,6-tetramethylpiperidine N-oxyl, ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl; NMI = N-methylimidazole), in acetonitrile are shown to have good long-term stability (≥1 year) under air at 5 °C. The solutions may be combined in appropriate quantities with commercially available [Cu(MeCN)4]OTf to provide a convenient catalyst system for the aerobic oxidation of primary and secondary alcohols.

Efficient magnetic and recyclable SBILC (supported basic ionic liquid catalyst)-based heterogeneous organocatalysts for the asymmetric epoxidation of trans-methylcinnamate

A green alternative, based on the use of an efficient and recyclable chiral ketone@SBILC@MWCNT@Fe3O4 catalytic system (Y = 35%, S = 100% and ee = 100%), was developed for the asymmetric epoxidation of trans-methylcinnamate to (2R,3S)

Highly efficient aerobic oxidation of alcohols by using less-hindered nitroxyl-radical/copper catalysis: Optimum catalyst combinations and their substrate scope

The oxidation of alcohols into their corresponding carbonyl compounds is one of the most fundamental transformations in organic chemistry. In our recent report, 2-azaadamantane N-oxyl (AZADO)/copper catalysis promoted the highly chemoselective aerobic oxidation of unprotected amino alcohols into amino carbonyl compounds. Herein, we investigated the extension of the promising AZADO/copper-catalyzed aerobic oxidation of alcohols to other types of alcohol. During close optimization of the reaction conditions by using various alcohols, we found that the optimum combination of nitroxyl radical, copper salt, and solution concentration was dependent on the type of substrate. Various alcohols, including highly hindered and heteroatom-rich ones, were efficiently oxidized into their corresponding carbonyl compounds under mild conditions with lower amounts of the catalysts.

Unprecedented 8,9′-neolignans: Enantioselective synthesis of possible stereoisomers for structural determination

(+)-Wutaienin (3) and its C-7 methyl ether (4), isolated from Zanthoxylum wutaiense, were found to be unprecedented 8,9′-neolignans containing an (S)-2-(1,1-dimethyl-1-hydroxymethyl)-7-methoxydihydrobenzofuran skeleton. Wutaienin (3) was present in the pl

Concise synthesis of chiral N -Benzyl-α,α-Diarylprolinols through shi asymmetric epoxidation

A concise and practical synthesis of chiral N-benzyl-α,α- diaryl-2-prolinols was developed through Shi asymmetric epoxidation, followed by double nucleophilic substitution of bromo-containing olefins. A series of enantioenriched N-benzyl-α,α-diaryl-2-prolinols were obtained with excellent enantioselectivities (96% ee) in moderate to good yields (40-76% yield). For the first time, enantiopure N-benzyl-α,α-diphenyl-2- prolinol was obtained from bromo-containing olefin using this methodology. Georg Thieme Verlag Stuttgart, New York.