54897-59-5Relevant academic research and scientific papers
Crystallization Does It All: An Alternative Strategy for Stereoselective Aza-Henry Reaction
Mar?eková, Michaela,Ger?a, Peter,?oral, Michal,Moncol, Ján,Berke?, Du?an,Kolarovi?, Andrej,Jakubec, Pavol
supporting information, p. 4580 - 4584 (2019/06/17)
An efficient and experimentally straightforward method for the stereoselective synthesis of a variety of β-nitro-α-amino carboxylic acids via aza-Henry (nitro-Mannich) reaction of aldimines is disclosed, yielding either anti- or a rarely reported syn-configuration. The reaction operates directly on free glyoxylic acid and generates imine species in situ. Crystallization-controlled diastereoselectivity enables isolation of the target compounds in high enantio- and diastereomeric purities by a simple filtration.
Tn Antigen Mimics by Ring-Opening of Chiral Cyclic Sulfamidates with Carbohydrate C1- S- and C1- O-Nucleophiles
Tovillas, Pablo,García, Iván,Oroz, Paula,Mazo, Nuria,Avenoza, Alberto,Corzana, Francisco,Jiménez-Osés, Gonzalo,Busto, Jesús H.,Peregrina, Jesús M.
, p. 4973 - 4980 (2018/05/17)
Starting from commercially available (S)-isoserine and effectively accessible (S)-α-methylserine, enantiopure cyclic sulfamidates have been prepared as chiral building blocks for the synthesis of various S- and O-glycosylated amino acid derivatives, inclu
Preparation method and application of D-dencichine
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Paragraph 0081; 0082, (2016/10/17)
The invention discloses a preparation method and application of D-dencichine. The preparation method comprises the following steps: carrying out Fmoc protection on the amino group of D-asparagine so as to obtain a first intermediate; subjecting the first intermediate to Hoffman degradation reaction so as to obtain a second intermediate; subjecting the second intermediate to removal of Fmoc protection under the action of organic base so as to obtain a third intermediate; and subjecting the third intermediate and monomethyl oxalate to condensation reaction under a highly basic condition so as to obtain D-dencichine. D-dencichine is prepared by using the high-efficiency safe preparation method; the preparation method is simple and has high yield; the compound D-dencichine prepared by using the method has good treatment effect on thrombocytopenia and the effect is better than the effect of a clinical medicine interleukin-11, so D-dencichine can be used as a candidate medicine for treating thrombocytopenia.
Bacterial preparation of enantiopure unactivated aziridine-2-carboxamides and their transformation into enantiopure nonnatural amino acids and vic-diamines
Moran-Ramallal, Roberto,Liz, Ramon,Gotor, Vicente
, p. 521 - 524 (2007/10/03)
Enantiopure (1R,2S)-1-benzyl- and 1-arylaziridine-2-carboxamides were obtained by kinetic resolution of their racemates by Rhodococcus rhodochrous IFO 15564 catalyzed hydrolysis. Several regio- and enantioselective nucleophilic ring openings of (1R,2S)-1-benzylaziridine-2-carboxamide or its LAH-reduced product led to a series of enantiopure products, such as O-methyl-L-serine and some vicinal diamines.
A new and facile route for the synthesis of chiral 1,2-diamines and 2,3-diamino acids
Nadir, Upender K.,Krishna, R. Vijaya,Singh, Anamika
, p. 479 - 482 (2007/10/03)
The synthesis of chiral diamines and diamino acids has been achieved from the corresponding N-arylsulfonyl aziridines through reaction with a chiral isocyanate and subsequent hydrolysis of 2-imidazolidinones. The method appears to be general and of wide applicability.
An improved stereoselective synthesis of L-alanosine
Strazzolini, Paolo,Dall'Arche, Maria Grazia,Zossi, Maura,Pavsler, Andrea
, p. 4710 - 4716 (2007/10/03)
An improved, stereoselective synthesis of the natural, non-proteogenic amino acid L-alanosine has been developed, starting from the readily available and cheap substrate L-serine, in six steps and 49% overall yield. The process is very efficient, is suitable for large-scale production, and affords L-alanosine with properties comparable with those of the natural substance. In addition, the structural assignment concerning some previously reported synthetic alkylated derivatives of the natural amino acid has been definitively confirmed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
Stereochemistry of Nucleophilic Ring-Opening Reactions of Optically Active N-Acetyl-2-Methoxycarbonylaziridine.
Davoli, Paolo,Forni, Arrigo,Moretti, Irene,Prati, Fabio
, p. 2011 - 2016 (2007/10/03)
The SN2-like mechanism of the nucleophilic attack of sodium azide on (S)-(-)-N-acetyl-2-methoxycarbonylaziridine was verified through the chemical correlation of the ring-opening products with (S)-(+)- or (R)-(-)-2,3-diaminopropanoic acid monohydrochloride.
Reaction of N-Benzoyl-2-bromoglycine Methyl Ester with Deprotonated Nitroalkanes: Synthesis of β-Nitro and α,β-Dehydro Amino Acid Derivatives
Burgess, Vicky A.,Easton, Christopher J.
, p. 1063 - 1070 (2007/10/02)
N-Benzoyl-2-bromoglycine methyl ester (1) reacted with the alkyl nitronates (2a-e) to give the corresponding β-nitro amino acid derivatives (4a-e).Elimination reactions of (4a-d) afforded the α,β-dehydro amino acid derivatives (5a-d).Treatment of the β-nitrovaline derivative (4b) with tributyltin hydride gave the valine derivative (8).Reduction of the β-nitroalanine derivative (4a) gave the β-aminoalanine derivative (9), characterized by hydrolysis to 2,3-diaminopropionic acid hydrochloride
