Carbohydrate cyclic acetal formation and migration

Clode, David M.

doi:10.1021/cr60322a002

Cited by 250 publications

(83 citation statements)

References 74 publications

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“…Acetals/ketals are the important compounds or intermediates in the steroid chemistry and synthetic carbohydrate [1,2]. In the synthesis, the acetals/ketals always need protection by 1,2-or 1,3-diols due to the high activity, which is commonly used in carbohydrate chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Besides, the acetals/ketals are used as intermediates and/or end products, in the phyto pharmaceutical, fragrances and lacquers industries [3,4]. They also have been used as solvents in many fields, such as cosmetics, detergent and lacquer industries [5], fragrance industries [6], pharmaceuticals [7], synthesis of enantiomerical compounds and polymer [8,9], beverage additives and food [10]. Acetals and its derivatives have also been used as additives in motor lubricating oils, and water based fluids of drilling petroleum operations [11].…”

Section: Introductionmentioning

confidence: 99%

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Structure and Antibacterial Activity of Bi-cyclohexanone Pentaerythritol Ketal

Huang¹

2016

Proceedings of the 2nd Annual International Conference on Advanced Material Engineering (AME 2016)

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Abstract. Cyclohexanone pentaerythritol ketal was synthesized from cyclohexanone and pentaerythritol by condensation using NaHSO 4 as catalyst and characterized by NMR and MS spectrum. Furthermore, the structure of the tile compound was confirmed by single-crystal X-ray diffraction. It crystallizes in orthorhombic space group, P 21, with a unit cell dimensions of a = 11.1214(9) Å, b = 13.9216(6) Å and c = 11.6658(10) Å. In the crystal, there are two independent molecules with different conformation, varying both in bond lengths and angles. In each molecular, there are four six-membered cycles, two cyclohexyl groups and two 1,3-dioxane groups. The four six-membered cycles all display a typical stable boat conformation. The stacking interaction is responsible for the crystal's 1-D supra-molecular structure. The thermal gravimetric analysis (TGA) indicates the title compound is stable below 200°C, and the remaining weight ratio is less than 9% above 300°C. This compound was evaluated for their in vitro antimicrobial activity against six bacteria (S. aureus, S. epidermidis, M. luteus, E. coli, K. pneumoniae, A. fumigatus). It some anti-inflammatory activity against the tested bacteria and the inhibition is depending on the concentration.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Structure and Antibacterial Activity of Bi-cyclohexanone Pentaerythritol Ketal

Huang¹

2016

Proceedings of the 2nd Annual International Conference on Advanced Material Engineering (AME 2016)

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“…This reaction is frequently employed to protect diols because acetals are stable under various conditions and can be removed by hydrolysis in the presence of acid. The preparation, chemistry, and physical properties of carbohydrates cyclic acetals have been reviewed 1 .…”

Section: Introductionmentioning

confidence: 99%

A High Yield Synthesis of 1,2:5,6-Di-O-Isopropylidene-D-Mannitol

Alvarenga¹,

Carneiro²,

Silvério³

et al. 2006

J. Chil. Chem. Soc.

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A HIGH YIELD SYNTHESIS OF 1,2:5,6-DI-O-ISOPROPYLIDENE-D-MANNITOL: A great improvement in the synthesis of 1,2:5,6-di-O-isopropylidene-D-mannitol (2) using D-mannitol (1) as starting material, is described. The acetalation of (Δ) was performed in acetone in the presence of zinc chloride as catalyst to give (2) in 87% yield. Some studies on the acetal stability were carried out to explain the high yields. High field NMR spectra were obtained and assignment of all signals was accomplished with the aid of double irradiation, difference NOE and HETCOR spectra.

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“…Besides the interest of acetal as protecting groups, many of them have found direct application as fragrances, in cosmetics, food and beverage additives, in pharmaceuticals, in detergents, in lacquer industry, and polymer chemistry [2,[3][4][5][6][7]. Also, the reaction is widely used for the synthesis of enantiomerically pure compounds [8].…”

mentioning

confidence: 99%

“…Solid acid catalysts are the best alternative. Solid acid catalysts reported for this reaction include; montmorillonite clay [10,11], mesoporous aluminosilicate [12], Ce-mont [13], sulphated metal oxides [14], cation exchanged resins [15], and acidic zeolites [2,6]. There are other protocols available for the protection of carbonyl compounds.…”

mentioning

confidence: 99%

Acetalization of ketones on K-10 clay and rare earth exchanged HFAU-Y zeolites: A mild and facile procedure for the synthesis of dimethylacetals

Thomas

Sugunan

2006

J Porous Mater

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Dimethylacetals of ketones; cyclohexanone, acetophenone, and benzophenone have been prepared by reacting ketones with methanol under mild reaction conditions. Large pore zeolites (H-Y and its rare earth metal, Ce 3+ , La 3+ , and RE 3+ modified forms), and mesoporous clay (K-10 montmorillonite and its cerium exchanged counterpart) with regular pore structure, silica and silica-alumina have been used as catalysts. Clay catalysts are found to be much more active than zeolites, thanks to slightly bigger pore size. The nature of the pores of the solid acid catalysts determine acetalization efficiency of a particular catalyst. As evidenced by the reaction time studies, the catalyst decay is greater over the zeolites than over the clays. Carrying out the reaction with ketones of different molecular sizes it is shown that K-10 clays and rare earth exchanged H-Y zeolites are promising environmentally friendly catalysts for their use in the production fine chemicals.

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Carbohydrate cyclic acetal formation and migration

Cited by 250 publications

References 74 publications

Structure and Antibacterial Activity of Bi-cyclohexanone Pentaerythritol Ketal

Structure and Antibacterial Activity of Bi-cyclohexanone Pentaerythritol Ketal

A High Yield Synthesis of 1,2:5,6-Di-O-Isopropylidene-D-Mannitol

Acetalization of ketones on K-10 clay and rare earth exchanged HFAU-Y zeolites: A mild and facile procedure for the synthesis of dimethylacetals

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