- Method for synthesizing 9-fluorenylmethylsuccinimido carbonate by one-pot two-phase method
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The invention relates to the technical field of organic synthesis, specifically to a method for synthesizing 9-fluorenylmethylsuccinimido carbonate by a one-pot two-phase method. The method comprisesthe following steps: adding purified water and hydroxylamine sulfate into a reaction container, dropwise adding liquid caustic soda under stirring, after the liquid caustic soda is dropwise added, adding butanedioic anhydride in batches, and carrying out high-temperature vacuum dehydration under acid catalysis until no water is extracted out so as to prepare an N-hydroxysuccinimide solution; adding a chloroformic acid-9-fluorenyl methyl ester solution into the N-hydroxysuccinimide solution, and controlling a temperature at 0 to 60 DEG C; after the chloroformic acid-9-fluorenyl methyl ester solution is added, starting to dropwise add an aqueous alkali solution; after the aqueous alkali solution is dropwise added, separating out an organic layer, carrying out concentrating to dryness, and carrying out recrystallizing so as to obtain a 9-fluorenylmethylsuccinimido carbonate finished product. The above-mentioned method provided by the invention innovatively adopts the one-pot two-phase method; a reaction liquid containing N-hydroxysuccinimide is directly used for synthesizing the 9-fluorenylmethylsuccinimido carbonate in a two-phase reaction manner; process steps are effectively reduced; and the method is applicable to large-scale industrial production.
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Paragraph 0011; 0024-0029
(2020/03/03)
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- Eight-membered ring-containing jadomycins: Implications for non-enzymatic natural products biosynthesis
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Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.
- Robertson, Andrew W.,Martinez-Farina, Camilo F.,Smithen, Deborah A.,Yin, Huimin,Monro, Susan,Thompson, Alison,McFarland, Sherri A.,Syvitski, Raymond T.,Jakeman, David L.
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supporting information
p. 3271 - 3275
(2015/03/30)
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- The two pathways for effective orthogonal protection of L-ornithine, for amino acylation of 5'-O-Pivaloyl nucleosides, describe the general and important role for the successful imitation, during the synthesis of the model substrates for the ribosomal mimic reaction
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Bz(NO2)-Orn(Boc)-OCH2CN was synthesized as an amino acid component with effective and successful orthogonal protection for amino acylation of 5'-O-Pivaloyl nucleosides and preparation of substrates for model ribosome reactions. The synthesis was carried out using suitable combinations of the methods of peptide synthesis and modification of amino acids.
- Bayryamov, Stanislav G.,Vassilev, Nikolay G.,Petkov, Dimiter D.
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experimental part
p. 889 - 898
(2011/12/14)
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- The study of the reaction of terminated oligomerization in the synthesis of oligo-(β1-6)-glucosamines
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The applicability of terminated oligomerization to the synthesis of oligo-(β1-6)-glucosamines, fragments of the intercellular polysaccharide adhesin of staphylococci, was studied. The reactions of terminated oligomerization were carried out with mono-, di-, and trisaccharide monomers and N-protected aminopropanol; and spacered mono-and disaccharides as terminating molecules were also attempted. The primary formation of cyclic products of monomer intramolecular glycosylation was observed in almost all the reactions. Only the experiments with the monomer based on the disaccharide bromide under the conditions of the Helferich reaction led to reduced yields (30%) of the cyclic products. However, even in this case, the desired terminated oligosaccharides were generated in approximately 10% yield and mainly were the products of single glycosylation of the terminator by the monomer. These experiments allow the conclusion that, under the examined conditions, the reaction of terminated oligomerization could not result in the synthesis of oligoglucosamines with a high molecular mass. Pleiades Publishing, Inc., 2006.
- Gening,Tsvetkov,Pier,Nifantiev
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p. 389 - 399
(2008/02/09)
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- High enantio-selective process for producing pure enantiomeric cyclopentane and cyclopentene-(β)-amino acids
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The present invention relates to a highly enantioselective process for the preparation of enantiomerically pure cyclopentane- and -pentene β-amino acids of the general formula (I) STR1 in which A and L, A and D or E and L, D and E, R2, R3, T and R1 have the meaning given in the description.
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- A large scale synthesis of mono- and di-urethane derivatives of lysine
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In the search for a practical route to lysine diurethane derivatives useful for peptide synthesis, we elaborated the synthesis of N(ε)-tert- butoxycarbonyl-L-lysine copper(II) complex (1). This served as substrate for obtaining N(ε)-tert-butoxycarbonyl-L-lysine (2), N(α)-benzyloxycarbonyl- N(ε)-tert-butoxycarbonyl-L-lysine dicyclohexylamine salt (3) and N(α)-(9- fluorenyl)methoxycarbonyl-N(ε)-tert-butoxycarbonyl-L-lysine (4).
- Wiejak, Stanislaw,Masiukiewicz, Elzbieta,Rzeszotarska, Barbara
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p. 1489 - 1490
(2007/10/03)
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- Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxyamino acids using succinimidyl carbonates
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9-Fluorenylmethyl succinimidyl, pentachlorophenyl, and benzotriazole-1-yl carbonates were prepared and their reactivity with L-serine and L-serine benzyl ester was compared.The most efficient reagent, 9-fluorenylmethyl succinimidyl carbonate, was used for the preparation of 9-flourenylmethyloxycarbonyl derivatives of other hydroxyamino acids and hydroxyamino acid esters in high yields.The use of trichloroethyl and benzyl succinimidyl carbonates for an efficient conversion of hydroxyamino acids and their esters into the corresponding N-trichloroethoxycarbonyl and benzyloxycarbonyl derivatives is described.
- Paquet, Alenka
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p. 976 - 980
(2007/10/02)
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