1152-61-0Relevant articles and documents
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Voelter,W. et al.
, p. 2649 - 2654 (1972)
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On the racemisation of aspartic anhydride during its preparation
Buron, Frederic,Deguest, Geoffrey,Bischoff, Laurent,Fruit, Corinne,Marsais, Francis
, p. 1625 - 1627 (2007)
Due to the possible differentiation of both carboxyl groups, N-protected aspartic anhydride is a useful starting material in synthesis. However, most methods published in the literature for its formation lead to partial racemisation, which is generally not mentioned. Herein we report a comparison between the main methods published, with accurate measurements of the enantiomeric purity of this compound.
Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles
Deguest, Geoffrey,Bischoff, Laurent,Fruit, Corinne,Marsais, Francis
, p. 2120 - 2125 (2006)
Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.
Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum-Polymer Conjugates
Tsai, Fu-Te,Wang, Yanyan,Darensbourg, Donald J.
supporting information, p. 4626 - 4633 (2016/05/19)
(S)-3,4-Dihydroxybutyric acid ((S)-3,4-DHBA), an endogenous straight chain fatty acid, is a normal human urinary metabolite and can be obtained as a valuable chiral biomass for synthesizing statin-class drugs. Hence, its epoxide derivatives should serve as promising monomers for producing biocompatible polymers via alternating copolymerization with carbon dioxide. In this report, we demonstrate the production of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) from racemic-tert-butyl 3,4-epoxybutanoate (rac-tBu 3,4-EB) and CO2 using bifunctional cobalt(III) salen catalysts. The copolymer exhibited greater than 99% carbonate linkages, 100% head-to-tail regioselectivity, and a glass-transition temperature (Tg) of 37 °C. By way of comparison, the similarly derived polycarbonate from the sterically less congested monomer, methyl 3,4-epoxybutanoate, displayed 91.8% head-to-tail content and a lower Tg of 18 °C. The tert-butyl protecting group of the pendant carboxylate group was removed using trifluoroacetic acid to afford poly(3,4-dihydroxybutyric acid carbonate). Depolymerization of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) in the presence of strong base results in a stepwise unzipping of the polymer chain to yield the corresponding cyclic carbonate. Furthermore, the full degradation of the acetyl-capped poly(potassium 3,4-dihydroxybutyrate carbonate) resulted in formation of the biomasses, β-hydroxy-γ-butyrolacetone and 3,4-dihydroxybutyrate, in water (pH = 8) at 37 °C. In addition, water-soluble platinum-polymer conjugates were synthesized with platinum loading of 21.3-29.5%, suggesting poly(3,4-dihydroxybutyric acid carbonate) and related derivatives may serve as platinum drug delivery carriers.
Synthesis and anticonvulsant evaluation of (R)-and (S)-3-carbobenzyloxy- amino-1-oxysuccinimides
Lee, Do-Hun
, p. 5948 - 5950 (2013/07/26)
A series of (R)-and (S)-3-carbobenzyloxy-amino-1-oxysuccinimides (5a-d) [(S)-3-carbobenzyloxy-amino-1-benzoyloxysuccinimde, (R)-3-carbobenzyloxy-amino- 1-acetyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1,4-nitrobenzoyloxysuccinimde, (R)-3-carbobenzyloxyamino-1,4-fluorobenzoyloxysuccinimde] were synthesized and investigated their anticonvulsant activities in maximal electric shock seizure test and pentylenetetrazole induced seizure test.
