cas 104597-98-0, 1-BENZYL 2-METHYL (S)-(-)-1,2-AZIRIDINEDICARBOXYLATE

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Synthesis of homochiral acyclic mono- and bis(α-amino acid)s with oligo(oxyethylene) chains
Synthesis of homochiral α-amino acids 3a-3e and bis(α-amino acid)s 4a-4e via BF3·Et2O-catalyzed ring-opening of methyl (S)-1-[(benzyloxy)carbonyl]aziridine-2-carboxylate (7) with oligo(ethylene glycol)s and subsequent acid hydrolysis
Belohradsky, Martin,Ridvan, Ludek,Zavada, Jiri
p. 1319 - 1325
(2003)
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IMMUNOPROTEASOME INHIBITORS
Provided herein are compounds, such as a compound of Formula (I), or a pharmaceutically acceptable salt thereof, that are immunoproteasome (such as LMP2 and LMP7) inhibitors. The compounds described herein can be useful for the treatment of diseases treatable by inhibition of immunoproteasomes. Also provided herein are pharmaceutical compositions containing such compounds and processes for preparing such compounds.
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Paragraph 0276

(2019/06/13)

Selective cleavage of carbamate protecting groups from aziridines with otera's catalyst
Otera's distannoxane catalyst was found to promote the cleavage of carbamate groups from N-protected aziridines. This method enables the chemoselective cleavage of an aziridinyl N-carbobenzyloxy (Cbz) group in the presence of other N-Cbz groups. The selec
Sun, Shan,Tirotta, Ilaria,Zia, Nicholas,Hutton, Craig A.
p. 411 - 415
(2014/04/03)

Diastereoselective aziridination of chiral electron-deficient olefins with N-chloro-N-sodiocarbamates catalyzed by chiral quaternary ammonium salts
Chiral quaternary ammonium salt-catalyzed diastereoselective aziridination of electron-deficient olefins that possess a chiral auxiliary with N-chloro-N-sodiocarbamates was developed. The key to high stereoselectivity was found to be the employment of the
Murakami, Yuta,Takeda, Youhei,Minakata, Satoshi
experimental part
p. 6277 - 6285
(2011/10/02)

Catalytic asymmetric aziridination of α,β-unsaturated aldehydes
The development, scope, and application of the highly enantioselective organocatalytic aziridination of α,β-unsaturated aldehydes is presented. The aminocatalytic azirdination of α,β-unsaturated aldehydes enables the asymmetric formation of β-formyl aziri
Deiana, Luca,Dziedzic, Pawel,Zhao, Gui-Ling,Vesely, Jan,Ibrahem, Ismail,Rios, Ramon,Sun, Junliang,Cordova, Armando
supporting information; experimental part
p. 7904 - 7917
(2011/08/05)

The in vitro transport of model thiodipeptide prodrugs designed to target the intestinal oligopeptide transporter, PepT1
A thiodipeptide carrier system is shown to be effective at enabling a range of covalently bound molecules, including benzyl, benzoyl and ibuprofen conjugates, to be transported via the intestinal peptide transporter PepT1, demonstrating its potential as a rational drug delivery target.
Foley, David,Pieri, Myrtani,Pettecrew, Rachel,Price, Richard,Miles, Stephen,Lam, Ho Kam,Bailey, Patrick,Meredith, David
supporting information; experimental part
p. 3652 - 3656
(2009/10/23)

Stereochemistry of reactions of the inhibitor/substrates L- And D-β-chloroalanine with β-mercaptoethanol catalysed by L-aspartate aminotransferase and D-amino acid aminotransferase respectively
Two members of the α-family of PLP-dependent enzymes, L-aspartate aminotransferase and D-amino acid aminotransferase, have been shown to catalyse β-substitution of L- and D-β-chloroalanine respectively with β-mercaptoethanol, reactions typical of the β-family of PLP-dependent enzymes. The reaction catalysed by L-aspartate aminotransferase has been shown to occur with retention of stereochemistry, a typical outcome for reactions catalysed by β-family enzymes. There are also indications that the reaction catalysed by D-amino acid aminotransferase may involve retention of stereochemistry. Both enzymes have been shown to catalyse exchange at C-3 when the appropriate enantiomer of β-chloroalanine is the substrate. The Royal Society of Chemistry 2005.
Adams, Benjamin,Lowpetch, Kreingkrai,Thorndycroft, Faye,Whyte, Sheena M.,Young, Douglas W.
p. 3357 - 3364
(2007/10/03)

Total synthesis and revision of stereochemistry of the marine metabolite trunkamide A
The isolation of the cytotoxic Lissoclinum sp. metabolite trunkamide A was reported in 1996. After completion of a total synthesis in 1999, it became clear that the structure of this marine natural product had to be revised. We now report the first preparation of actual trunkamide A in a total synthesis that serves as an unambiguous structural and stereochemical proof. Highlights of our synthetic strategy are a Lewis acid assisted aziridine opening that was used for the preparation of the novel reverse- prenylated serine and threonine side chains as well as an efficient oxazoline-thiazoline interconversion on the macrocyclic skeleton. In addition, several stereoisomers prepared by complementary synthetic protocols serve to illustrate the general scope of our methodology and confirm the configurational assignment.
Wipf, Peter,Uto, Yoshikazu
p. 1037 - 1049
(2007/10/03)

Efficient synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)-hexahydro-1H-1,4-diazepine from methyl (2R)- and (2S)-1-benzyloxycarbonylaziridine-2-carboxylates
An efficient and practical method for the synthesis of (6R)-6-amino-1-methyl-4-(3-methylbenzyl)hexahydro-1H-1,4-diazepine 2, which serves as the amine part of DAT-582, a potent and selective 5-HT3 receptor antagonist, is described. The key inte
Kato, Shiro,Harada, Hiroshi,Morie, Toshiya
p. 3219 - 3225
(2007/10/03)

CONSTRUCTION OF OPTICALLY PURE TRYPTOPHANS FROM SERINE DERIVED AZIRIDINE-2-CARBOXYLATES
The possibility of preparing optically pure tryptophan derivatives from various substituted indoles and (2R)- or (2S)-2-aziridinecarboxylates has been examined.Zinc triflate was found to be the only Lewis acid capable of bringing about this reaction in mo
Sato, Kazuo,Kozikowski, Alan P.
p. 4073 - 4076
(2007/10/02)

Chemical Properties

Boiling Point: 343.4°Cat760mmHg
Flash Point:161.5°C
Density: 1.305g/cm³
Solubility:Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane
Storage Temp.:Sealed in dry,Store in freezer, under -20°C
Vapor Pressure: 7.04E-05mmHg at 25°C
Refractive Index: n20/D 1.519(lit.)
PKA: -5.65±0.40(Predicted)
PSA: 55.61000
LogP: 1.11830

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Chemical Properties

Boiling Point: 343.4°Cat760mmHg

Flash Point:161.5°C

Density: 1.305g/cm³

Solubility:Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane

Storage Temp.:Sealed in dry,Store in freezer, under -20°C

Vapor Pressure: 7.04E-05mmHg at 25°C

Refractive Index: n20/D 1.519(lit.)

PKA: -5.65±0.40(Predicted)

PSA: 55.61000

LogP: 1.11830

Global suppliers and manufacturers of 104597-98-0total 26 suppliers on LookChem

Article Database

104597-98-0

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Chemical Properties

Boiling Point: 343.4°Cat760mmHg

Flash Point:161.5°C

Density: 1.305g/cm3

Solubility:Chloroform (Slightly), DMSO (Slightly), Methanol (Soluble), Dichloromethane

Storage Temp.:Sealed in dry,Store in freezer, under -20°C

Vapor Pressure: 7.04E-05mmHg at 25°C

Refractive Index: n20/D 1.519(lit.)

PKA: -5.65±0.40(Predicted)

PSA: 55.61000

LogP: 1.11830

Global suppliers and manufacturers of 104597-98-0total 26 suppliers on LookChem

Density: 1.305g/cm³