111652-20-1Relevant articles and documents
Synthesis of regio- and stereoselectively deuterium-labelled derivatives of l-glutamate semialdehyde for studies on carbapenem biosynthesis
Ducho, Christian,Hamed, Refaat B.,Batchelar, Edward T.,Sorensen, John L.,Odell, Barbara,Schofield, Christopher J.
, p. 2770 - 2779 (2009)
l-Glutamate semialdehyde (l-GSA) is an intermediate in biosynthetic pathways including those leading to the carbapenem antibiotics. We describe studies on asymmetric deuteration or hydrogenation of appropriate didehydro-amino acid precursors for the stereoselective synthesis of C-2- and/or C-3-[2H]-labelled l-GSA suitable for use in mechanistic studies. Regioselective deuterium incorporation into the 5-position of l-GSA was achieved using a labelled form of the Schwartz reagent (Cp2Zr 2HCl). 4,4-Dideuterated and fully backbone deuterated l-GSAs were prepared. The application of the labelled l-GSA derivatives to biosynthetic studies was exemplified by the chemo-enzymatic preparation of selectively deuterated trans-carboxymethylprolines using two different carboxymethylproline synthases (CarB and ThnE), enzymes that catalyse early steps in the biosynthesis of two carbapenems: (5R)-carbapenem-3-carboxylate and thienamycin, respectively. The Royal Society of Chemistry 2009.
Transformation of azido-group to N-(t-butoxycarbonyl)amino group under mild conditions via Staudinger reaction
Afonso, Carlos A. M.
, p. 8857 - 8858 (1995)
In a convenient simple sequence, treatment of azides with tri-n-butylphosphine, followed by addition of di-t-butyl dicarbonate, yields N-(t-Butoxycarbonyl)amines in moderate to good overall yields.
Studies on the transformation of azido-group to N-(t-butoxycarbonyl)amino group via Staudinger reaction
Afonso, Carlos A. M.
, p. 261 - 276 (1998)
By a simple and direct sequence, treatment of primary azides with tri-n-butylphosphine, followed by addition of di-t-butyl dicarbonate (Boc2O) affords, N-(t-Butoxycarbonyl)amines 2 in moderate to good overall yields. For secondary azides the fo
Single Electron Transfer-Induced Selective α-Oxygenation of Glycine Derivatives
Venugopal, Navyasree,Moser, Johannes,Vojtí?ková, Margaréta,Císa?ová, Ivana,K?nig, Burkhard,Jahn, Ullrich
supporting information, p. 405 - 412 (2021/11/03)
Modification of amino acids is an important strategy in organic and bioorganic chemistry. In contrast to common side-chain functionalization, backbone modification is much less explored. Especially glycine units seem to be attractive and versatile since a wide range of functionality can be potentially introduced. We report here oxidative modification of glycinates that are stable and enable further functionalization. Selective glycinate enolate oxidation by TEMPO or a FeCp2PF6/TEMPO reagent combination provides stable alkoxyamines in good to excellent yields. The methodology is expanded to glycine-containing dipeptides demonstrating selective oxygenation at the glycine unit. The orthogonal reactivity potential of oxygenated glycines for transformation to other amino acid derivatives is explored.
Preparation method of tert-butyl glycine
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Paragraph 0037-0039, (2021/11/06)
The invention discloses a preparation method of tert-butyl glycine, and belongs to the technical field of organic synthesis. The raw materials are easily available, the process is simple, the process is simple, the reaction conditions are mild, the requirement for equipment is low, the total yield is up to 85 - 93%, and a significant amount of double-substituted by-products are effectively avoided in the direct reaction with ammonia in the traditional process.
TRANSESTERIFICATION REACTION BY MEANS OF IRON CATALYST
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Paragraph 0134; 0135; 0142; 0143, (2017/10/10)
Provided is a catalyst for transesterification reactions, which contains an iron salen complex. Also provided is a method for producing an ester compound, which is characterized by carrying out a transesterification reaction between a starting material ester and a starting material alcohol with use of the catalyst.
Diamine precursor process for the production of compounds
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Paragraph 0119; 0120; 0121; 0122; 0123; 0124, (2016/10/07)
Provided is an inexpensive, simple, and efficient method for preparing, from a starting material, a nitro compound constituting a diamine precursor compound which is a starting material for producing a polyamic acid and/or polyimide. Compound (1) is reacted according to reaction formula (1) with di-tert-butyl dicarbonate ((Boc)2O) to produce compound (2) (1) (where R1 represents -CH2COOR or -CH2Ph(-Z)m (where Z is a substituent group for a phenyl group (Ph) and m ranges from 0 to 5), and R represents a lower alkyl group or alkali metal atom), compound (2) is then reacted according to reaction formula (2) with H-A-CH2-X to produce compound (3) (2) (where A represents -C=C- or -CH=CH-, and X represents a leaving substituent group), and compound (3) is then subjected to a coupling reaction according to reaction formula (3) with compound (4) to produce compound (5) (3) (where Y represents a leaving substituent group).
μ-Oxo-Dinuclear-Iron(III)-Catalyzed O-Selective Acylation of Aliphatic and Aromatic Amino Alcohols and Transesterification of Tertiary Alcohols
Horikawa, Rikiya,Fujimoto, Chika,Yazaki, Ryo,Ohshima, Takashi
supporting information, p. 12278 - 12281 (2016/08/24)
A highly chemoselective and reactive μ-oxo-dinuclear iron(III) salen catalyst for transesterification was developed. The developed iron complex catalyzed acylation of aliphatic amino alcohols with nearly perfect O-selectivity, even when using activated esters, for which chemoselectivity is more difficult to control. In addition, O-selective transesterification of aromatic amino alcohols was achieved for the first time. The high activity of the iron complex enabled the use of sterically congested tertiary alcohols, including unprecedented tert-butanol.
Molecular discrimination of N-protected amino acid esters by a self-assembled cylindrical capsule: spectroscopic and computational studies.
Hayashida, Osamu,Sebo, Lubomir,Rebek Jr., Julius
, p. 8291 - 8298 (2007/10/03)
A self-assembled, cylindrical capsule was used to bind N-alpha-protected amino acid esters. The reversible encapsulation was studied using NMR spectroscopy in deuterated mesitylene solution and by computer-aided molecular modeling. BOC-L-alanine alkyl est
N-alkyloxycarbonyl-3-aryloxaziridines: Their preparation, structure, and utilization as electrophilic amination reagents
Vidal, Joelle,Damestoy, Stephanie,Guy, Laure,Hannachi, Jean-Christophe,Aubry, Andre,Collet, Andre
, p. 1691 - 1709 (2007/10/03)
This paper reports the synthesis of a series of N-protected oxaziridines (N-Moc, Boc, Z or Fmoc) and discusses their ability to deliver their N-alkoxycarbonyl fragment to amines, enolates, sulfur, and phosphorus nucleophiles (electrophilic amination). These oxaziridines are prepared by oxidation of the corresponding imines with oxone or anhydrous MCPBA lithium salt as the source of oxygen. They transfer their N-protected fragment to primary and secondary amines to give protected hydrazines in fair to excelent yield. The nitrogen transfer to free amino acids (in form of their R4N+ salts) is particularly fast, even at low temperature, providing L (or D) N-protected α-hydrazino acids. Enolates are C-aminated to give N-protected α-amino ketones, esters, or amides in modest yield, due to a side aldol reaction of the unreacted enolate with the released benzaldehyde. With tertiary amines (Et3N), sulfides (PhSMe), and phosphines (Ph3P), amination and oxidation proceed in a parallel way; the amount of amination product increases when the temperature is lowered (kinetic control). Some of the factors that can orient the oxaziridine reactivity towards amination or oxidation of nucleophiles are considered.
