82494-08-4Relevant academic research and scientific papers
Simple preparation method of alkyl maltoside surfactant
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, (2020/06/09)
The invention belongs to the technical field of fine chemicals, and specifically discloses a preparation method of sugar-based nonionic surfactant alkyl-beta-D-maltoside. The preparation method includes the steps of performing an acylation reaction on maltose to obtain octa-O-acetyl-D-maltose, performing condensation on the octa-O-acetyl-D-maltose and fatty alcohol, and performing deprotection toobtain the alkyl-beta-D-maltoside. The preparation method provided by the invention is simple and easy to implement, has the advantages of mild and controllable conditions, low costs, and practicability.
Solution Properties of Alkyl β-D-Maltosides
Li, Zhencao,Chen, Guoyong,Chen, Langqiu,Zhang, Yanhua,Dai, Zhiyong
, p. 731 - 742 (2019/04/10)
Alkyl β-D-maltosides are an important class of sugar-based nonionic surfactants and have been widely studied. Nevertheless, it is still necessary to investigate further their amphiphilic structure-surface property relationships. In this article, we reported a series of properties of synthetic alkyl β-D-maltosides (6a–6i, n = 6–18) including their hydrophilic–lipophilic balance (HLB) number, water solubility, hygroscopicity, moisture-retention capacity, foaming ability, surface tension, thermotropic phase behavior, and skin irritation. Their HLB number and water solubility decreased with increasing alkyl chain length. Hexyl β-D-maltoside exhibited the strongest hygroscopicity and moisture-retention capacity. Decyl β-D-maltoside and dodecyl β-D-maltoside possessed excellent foaming power and foaming stability. Furthermore, the critical micelle concentration (CMC) of alkyl β-D-maltoside (6a–6g, n = 6–14) and their surface tension at CMC decreased with increasing alkyl chain length. At last, alkyl β-D-maltosides (6a–6g) should be considered as safe surfactants by the skin irritation assessment.
Synthesis of C7-C16-Alkyl maltosides in the presence of tin(IV) chloride as a lewis acid catalyst
Markovic, Zoran,Predojevic, Jasmina,Manojlovic, Nedeljko T.
experimental part, p. 83 - 90 (2012/05/20)
The synthesis of C7- to C16-alkyl maltosides in the presence of tin(IV) chloride as Lewis acid catalyst was performed. The characterization of the products and theoretical investigation of the crucial step in the synthesis were carried out. The preparation of the β-maltosides required reaction time of 1 h, and that of the α-maltosides was 72 h. The side products were the α-D-maltosidechloride and 2-hydroxy-β-maltoside, respectively. The PM3 calculation confirmed the formation of the kinetically controlled β-product.
Cyclomaltodextrin glucanotransferase-catalyzed transglycosylation from dextrin to alkanol maltosides
Zhao, Haisuo,Naito, Hiroyuki,Ueda, Yoshimi,Okada, Katsuhide,Sadagane, Kenji,Izumi, Minoru,Nakajima, Shuhei,Baba, Naomichi
scheme or table, p. 3006 - 3010 (2009/04/07)
Maltosides of butanol, octanol, and lauryl alcohol were found for the first time to serve as substrates for cyclomaltodextrin glucanotransferase (CGTase), and glycosyl residue was transfered from dextrin to the substrate affording novel maltosides with 3-
Simple preparations of alkyl and cycloalkyl α-glycosides of maltose, cellobiose, and lactose
Koto, Shinkiti,Hirooka, Motoko,Tashiro, Takako,Sakashita, Motokazu,Hatachi, Masaharu,Kono, Takayuki,Shimizu, Miho,Yoshida, Nahoko,Kurasawa, Sayaka,Sakuma, Natsuko,Sawazaki, Sunao,Takeuchi, Akihiro,Shoya, Naomi,Nakamura, Emi
, p. 2415 - 2424 (2007/10/03)
Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared via direct reaction of the free bioses with a binary AcBr-AcOH system, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and the chromatographic resolution of the mixture. The respective β-biosides were obtained via the glycosidation in MeCN. Alkyl, cycloalkyl, allyl, 4-pentenyl, and benzyl α-glycosides of maltose, cellobiose, and lactose were prepared (17-77% yield; α/β = 70/30-96/4) via a direct reaction of the free disaccharides with a binary AcBr-AcOH mixture, followed by glycosidation with alcohol using FeCl3 in MeNO2 or CH2Cl2, Zemple?n deacetylation, and resolution of the anomeric mixture of glycosides by chromatography. Using MeCN as solvent for the glycosidation step, the corresponding β-biosides were also prepared (16-61% yield; α/β = 25/75-5/95).
Optically active cyclophane receptors for mono- and disaccharides: The role of bidentate ionic hydrogen bonding in carbohydrate recognition
Droz, Anne Sophie,Neidlein, Ulf,Anderson, Sally,Seiler, Paul,Diederich, Francois
, p. 2243 - 2289 (2007/10/03)
A new family of optically active cyclophane receptors for the complexation of mono- and disaccharides in competitive protic solvent mixtures is described. Macrocycles (-)-(R,R,R,R)-1-4 feature preorganized binding cavities formed by four 1,1′-binaphthalene-2,2′-diyl phosphate moieties bridged in the 3,3′-positions by acetylenic or phenylacetylenic spacers. The four phosphodiester groups converge towards the binding cavity and provide efficient bidentate ionic H-bond acceptor sites (Fig. 2). Benzyloxy groups in the 7,7′-positions of the 1,1′-binaphthalene moieties ensure solubility of the nanometer-sized receptors and prevent undesirable aggregation. The construction of the macrocyclic framework of the four cyclophanes takes advantage of Pd0-catalyzed aryl-acetylene cross-coupling by the Sonogashira protocol, and oxidative acetylenic homo-coupling methodology (Schemes 2 and 8-10). Several cleft-type receptors featuring one 1,1′-binaphthalene-2,2′-diyl phosphate moiety were also prepared (Schemes 1, 6, and 7). An undesired side reaction encountered during the synthesis of the target compounds was the formation of naptho[b]furan rings from 3-ethynylnaphthalene-2-ol derivatives, proceeding via 5-endo-dig cyclization (Schemes 3-5). Computer-assisted molecular modeling indicated that the macrocycles prefer nonplanar puckered, cyclobutane-type conformations (Figs. 7 and 8). According to these calculations, receptor (-)-(R,R,R,R)-1 has, on average, a square binding site, which is complementary in size to one monosaccharide. The three other cyclophanes (-)-(R,R,R,R)-2-4 feature, on average, wider rectangular cavities, providing a good fit to one disaccharide, while being too large for the complexation of one monosaccharide. This substrate selectivity was fully confirmed in 1H-NMR binding titrations. The chiroptical properties of the cyclophanes and their nonmacrocyclic precursors were investigated by circular dichroism (CD) spectroscopy. The CD spectra of the acyclic precursors showed a large dependence from the number of 1,1′-binaphthalene moieties (Fig. 9), and those of the cyclophanes were remarkably influenced by the nature of the functional groups lining the macrocyclic cavity (Fig. 11). Profound differences were also observed between the CD spectra of linear and macrocyclic tetrakis(1,1′-binaphthalene) scaffolds, which feature very different molecular shapes (Fig. 10). In 1H-NMR binding titrations with mono- and disaccharides (Fig. 13), concentration ranges were chosen to favor 1:1 host - guest binding. This stoichiometry was experimentally established by the curve-fitting analysis of the titration data and by Job plots. The titration data demonstrate conclusively that the strength of carbohydrate recognition is enhanced with an increasing number of bidentate ionic host - guest H-bonds (Table 1) in the complex formed. As a result of the formation of these highly stable H-bonds, carbohydrate complexation in competitive protic solvent mixtures becomes more favorable. Thus, cleft-type receptors (-)-(R)-7 and (-)-(R)-38 with one phosphodiester moiety form weak 1:1 complexes only in CD3CN. In contrast, macrocycle (-)-(R,R,R,R)-1 with four phosphodiester groups undergoes stable inclusion complexation with monosaccharides in CD3CN containing 2% CD3OD. With their larger number of H-bonding sites, disaccharide substrates bind even more strongly to the four phosphodiester groups lining the cavity of (-)-(R,R,R,R)-2 and complexation becomes efficient in CD3CN containing 12% CD3OD. Finally, the introduction of two additional methyl ester residues further enhances the receptor capacity of(-)-(R,R,R,R)-3, and efficient disaccharide complexation occurs already in CD3CN containing 20% CD3OD.
