Synthesis of 2-modified 1,3-diacylglycerols

Haftendorn, Regine; Ulbrich‐Hofmann, Renate

doi:10.1016/0040-4020(94)01013-p

Cited by 19 publications

(10 citation statements)

References 11 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[14] We performed a base-mediated deprotection of the corresponding b-succinimide alcohol 6 obtaining a yield of 71 % of the amino alcohol 7 (Scheme 6).…”

Section: Resultsmentioning

confidence: 99%

“…1 H NMR d = 9.68 (s, 1 H), 1 H),2 H),3.19 (ddd,J = 1.7,9.1,17.7 Hz,1 H),2.90 (ddd,J = 1.0,5.3,17. d = 199.5, 177.1, 60.2, 45.3, 44.2, 34.2, 27.9, 25.8, 18.2 1, 59.6, 49.8, 34.0, 31.1, 29.0, 27.9, 26.5, 22.5, 14.0 1.28 (m, 12 H), 0.88 ppm (t, J 6.9 Hz, 3 H); 13 C NMR: d = 62.8,53.0,39.8,37.4,31.8,29.5,29.2,25.8,22.6,14.1 ppm; HRMS: m/z: calcd for C 10 H 24 NO: 174.1852 [M+H] + ; found: 174.1843.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Jiang

Nielsen

et al. 2007

Chemistry A European J

View full text Add to dashboard Cite

An easy and affordable route for obtaining chiral beta-aminated- and alpha,beta-diaminated aldehydes, 1,3-aminoalcohols, and related compounds by using organocatalysis is presented. The chiral secondary amine (S)-2-[bis(3,5-bistrifluoromethylphenyl)trimethylsilanyloxymethyl]pyrrolidine is used as the catalyst to activate alpha,beta-unsaturated aldehydes, which allows succinimide to add in a 1,4-regio- and stereoselective fashion thereby forming N-protected 1,3-aminoaldehydes in good yields and enantioselectivities. This is followed by two easy transformations giving rise to optically active 1,3-aminoalcohols, a common motif in many biologically active compounds, for example, fibrinogen receptor antagonists. Furthermore, optically active alpha,beta-syn-diaminated aldehydes were obtained by the addition of diethyl azodicarboxylate in a one-pot reaction.

show abstract

“…[14] We performed a base-mediated deprotection of the corresponding b-succinimide alcohol 6 obtaining a yield of 71 % of the amino alcohol 7 (Scheme 6).…”

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Jiang

Nielsen

et al. 2007

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…DAG has been utilized as a cocoa butter blooming agent (2) and as an intermediate in the synthesis of structural lipids (3,4). Recent studies on the nutritional properties and dietary effects of DAG (5)(6)(7)(8) have revealed that DAG, of which 1,3-DAG is a major component, in contrast to TAG, had the ability to reduce serum TAG concentrations (5) and, as a result, to decrease both body weight and visceral fat mass (6).…”

mentioning

confidence: 98%

Optimization of reaction conditions for the production of DAG using immobilized 1,3‐regiospecific lipase lipozyme RM IM

Watanabe

Shimizu

Sugiura

et al. 2003

J Americ Oil Chem Soc

158

View full text Add to dashboard Cite

Oils with a high DAG (1,3-DAG) content have attracted considerable attention as a healthful food oil component. In this study, we report on the synthesis of 1,3-DAG from a mixture of FA, constituted largely of oleic and linoleic acids, using an immobilized 1,3-regioselective lipase from Rhizomucor miehei in a solvent-free system. The kinetics of 1,3-DAG production from FA and glycerol were investigated on the basis of a simplified model, taking into consideration the acyl migration reaction, the removal of water, and glycerol dissolution in the oil phase in addition to the esterification reactions. Both the yield of 1,3-DAG and the purity of DAG were evaluated under a variety of experimental conditions, including reaction temperature, pressure, and amount of enzyme present. When either the reaction temperature or the amount of enzyme used was increased, the 1,3-DAG production rate increased, but yield remained relatively constant. The 1,3-DAG yield as well as the purity of DAG gradually decreased because of the enhancement of acyl migration at later stages of the reaction after the 1,3-DAG concentration reached a maximum. Vacuum was important for attaining high yields of 1,3-DAG. Under conditions of a high vacuum (1 mm Hg) at 50°C, 1.09 M 1,3-DAG was produced from 1.29 M glycerol and 2.59 M FA in an 84% yield and in 90% purity.Rate constants k 1 = 7.50 × 10 −4 (L/mol/s) k 3 = 2.91 × 10 −4 (L/mol/s) k 5 = 7.85 × 10 −6 (1/s) k 7 = 1.84 × 10 −3 (L/mol/s) k 9 = 3.59 × 10 −4 (1/s) k 10 = 1.20 × 10 −2 (1/s)

show abstract

“…Besides their use as nonionic surfactants in food, cosmetics, and pharmaceutical industries, 1,3-diacylglycerols (1,3-DAG) are intermediates for synthesis of various chemical compounds with pharmaceutical applications (1,2). Diglyceride prodrugs can be obtained when the second position is esterified with a drug bearing a carboxylic group such as the antiinflammatory niflumic acid (3), by covalently binding an alcohol, for example the β-blocker bupranolol (4), or phenytoin (5) to 2-chlorosuccinyl-1,3-diacylglycerol, etc.…”

mentioning

confidence: 99%

Enzymatic synthesis of symmetrical 1,3‐diacylglycerols by direct esterification of glycerol in solvent‐free system

Rosu

Yasui

Iwasaki

et al. 1999

J Americ Oil Chem Soc

107

View full text Add to dashboard Cite

1,3-Diacylglycerols were synthesized by direct esterification of glycerol with free fatty acids in a solvent-free system. Free fatty acids with relatively low melting points (<45°C) such as unsaturated and medium-chain saturated fatty acids were used. With stoichiometric ratios of the reactants and water removal by evaporation at 3 mm Hg vacuum applied at 1 h and thereafter, the maximal 1,3-diacylglycerol content in the reaction mixture was: 84.6% for 1,3-dicaprylin, 84.4% for 1,3-dicaprin, 74.3% for 1,3-dilinolein, 71.7% for 1,3-dieicosapentaenoin, 67.4% for 1,3-dilaurin, and 61.1% for 1,3-diolein. Some of the system's parameters (temperature, water removal, and molar ratio of the reactants) were optimized for the production of 1,3-dicaprylin, and the maximal yield reached 98%. The product was used for the chemical synthesis of 1,3-dicapryloyl-2-eicosapentaenoylglycerol. The yield after purification was 42%, and the purity of the triacylglycerol was 98% (both 1,3-dicapryloyl-2-eicosapentaenoylglycerol and 1,2-dicapryloyl-3-eicosapentaenoylglycerol included) by gas chromatographic analysis, of which 90% was the desired structured triacylglycerol (1,3-dicapryloyl-2-eicosapentaenoylglycerol) as determined by silver ion high-performance liquid chromatographic analysis.

show abstract

Synthesis of 2-modified 1,3-diacylglycerols

Cited by 19 publications

References 11 publications

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Organocatalysed Asymmetric β‐Amination and Multicomponent syn‐Selective Diamination of α,β‐Unsaturated Aldehydes

Optimization of reaction conditions for the production of DAG using immobilized 1,3‐regiospecific lipase lipozyme RM IM

Enzymatic synthesis of symmetrical 1,3‐diacylglycerols by direct esterification of glycerol in solvent‐free system

Contact Info

Product

Resources

About