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L-TERT-LEUCINE METHYLAMIDE is a chemical compound derived from the amino acid leucine, characterized by its chiral nature and unique structural properties. It serves as a chiral auxiliary in organic chemistry and is utilized in peptide synthesis, playing a significant role in the development of novel drug molecules and the creation of complex organic molecules.

89226-12-0

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89226-12-0 Usage

Uses

Used in Organic Chemistry:
L-TERT-LEUCINE METHYLAMIDE is used as a chiral auxiliary for its ability to influence the stereochemistry of chemical reactions, facilitating the synthesis of enantiomerically pure compounds.
Used in Peptide Synthesis:
L-TERT-LEUCINE METHYLAMIDE is used as a building block in the synthesis of peptides, contributing to the development of pharmaceuticals and other bioactive molecules.
Used in Pharmaceutical Development:
L-TERT-LEUCINE METHYLAMIDE is used as a precursor in the development of novel drug molecules, leveraging its chiral properties to create new therapeutic agents.
Used in Catalyst Design:
L-TERT-LEUCINE METHYLAMIDE is used as a potential catalyst in various chemical reactions, taking advantage of its unique structural properties to enhance reaction efficiency and selectivity.
Used in Fine Chemicals Synthesis:
L-TERT-LEUCINE METHYLAMIDE is used as a key component in the synthesis of fine chemicals, where its chiral nature is crucial for producing high-quality specialty chemicals.

Check Digit Verification of cas no

The CAS Registry Mumber 89226-12-0 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,9,2,2 and 6 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 89226-12:
(7*8)+(6*9)+(5*2)+(4*2)+(3*6)+(2*1)+(1*2)=150
150 % 10 = 0
So 89226-12-0 is a valid CAS Registry Number.
InChI:InChI=1/C7H16N2O/c1-7(2,3)5(8)6(10)9-4/h5H,8H2,1-4H3,(H,9,10)/t5-/m1/s1

89226-12-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-amino-N,3,3-trimethylbutanamide

1.2 Other means of identification

Product number -
Other names 2-azanyl-N,3,3-trimethyl-butanamide

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:89226-12-0 SDS

89226-12-0Downstream Products

89226-12-0Relevant articles and documents

Auxiliary-controlled diastereoselective synthesis of a syn C-6-epimer of the ADAM 10 inhibitor GI254023X

Nair, Shankari,Zeevaart, Jan Rijn,Hunter, Roger

, p. 90 - 102 (2020/10/08)

ADAM10 is a cell surface-expressed metalloprotease involved in various cell adhesion and proteolytic processes, in which biological studies have linked an over-expression of ADAM10 to the development and progression of various types of diseases including cancer. GI254023X is a hydroxamate metalloprotease inhibitor known for ADAM10 activity inhibition, but for which structure-activity based biological information for assessing anti-tumour and anti-inflammatory activity is lacking. In this work, an Evans’ asymmetric boron aldol reaction was used to synthesise a syn C-6-epimer of GI254023X intended for biological evaluation against the natural inhibitor.

A Bifunctional Photoaminocatalyst for the Alkylation of Aldehydes: Design, Analysis, and Mechanistic Studies

Rigotti, Thomas,Casado-Sánchez, Antonio,Cabrera, Silvia,Pérez-Ruiz, Raúl,Liras, Marta,De La Pe?a O'Shea, Víctor A.,Alemán, José

, p. 5928 - 5940 (2018/05/29)

A bifunctional photoaminocatalyst based on imidazolidinone and thioxanthone is presented. The preparation of these catalysts proceeds in a two-step synthesis that allows an easy tuning of the steric properties. The photophysical and electrochemical data of the imidazolidinone photocatalysts have been determined, indicating that the catalysts can work under visible light conditions. To corroborate the experimental observations, ground state geometry optimization and energy transition studies of thioxanthone and bifunctional catalyst 4c were optimized by time-dependent density functional theory (TD DFT) calculations. The alkylation of aldehydes with this photoaminocatalyst works with high enantioselectivities and yields due to the stereoelectronic properties of the catalyst. A rational mechanistic cycle based on different mechanistic experiments, TD DFT calculations, and laser flash photolysis is presented.

l-tert-Leucine-Derived AmidPhos-Silver(I) Chiral Complexes for the Asymmetric [3+2] Cycloaddition of Azomethine Ylides

Zhou, Zhipeng,Zheng, Xiaojun,Liu, Jialin,Li, Jinlei,Wen, Pushan,Wang, Haifei

, p. 999 - 1003 (2017/05/05)

The l-tert-leucine-derived AmidPhos/silver(I) catalytic system has been developed for the asymmetric [3+2] cycloaddition of azomethine ylides with electronic-deficient alkenes with or without Et3N. Under optimal conditions, highly functionalized endo-4-pyrrolidines were obtained with modest to high yields (up to 99% yield) and enantioselectivities (up to 98% ee).

Enantioselective α-Alkylation of Aldehydes by Photoredox Organocatalysis: Rapid Access to Pharmacophore Fragments from β-Cyanoaldehydes

Welin, Eric R.,Warkentin, Alexander A.,Conrad, Jay C.,MacMillan, David W. C.

supporting information, p. 9668 - 9672 (2015/08/11)

The combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective α-cyanoalkylation of aldehydes. This synergistic catalysis protocol allows for the coupling of two highly versatile yet orthogonal functionalities, allowing rapid diversification of the oxonitrile products to a wide array of medicinally relevant derivatives and heterocycles. This methodology has also been applied to the total synthesis of the lignan natural product (-)-bursehernin. A combination of photoredox catalysis and enamine catalysis has enabled the development of an enantioselective cyanoalkylation of aldehydes. This synergistic catalysis protocol makes possible the coupling of two highly versatile yet orthogonal functionalities.

Stereoselective nucleophilic addition to imines catalyzed by chiral bifunctional thiourea organocatalysts

Puglisi, Alessandra,Benaglia, Maurizio,Annunziata, Rita,Rossi, Davide

experimental part, p. 2258 - 2264 (2009/04/04)

A new and easy synthesis of chiral bifunctional organic catalysts obtained by the combination of (S)-t-leucine-derivatives with (1R,2R)-trans-1,2-diamino-cyclohexane was developed. A few compounds, representatives of a class of organocatalysts containing a thiourea group and a tertiary amino group connected through a chiral backbone, have been successfully synthesized. The catalytic behaviour of such bifunctional chiral molecules, either neutral or protonated species, was investigated in the addition of acetylacetone to β-nitrostyrene as a model reaction. Using the best conditions, high yields and enantioselectivities of up to 85% were obtained. The same metal free catalysts were then employed in the addition of activated nucleophiles to imines: in the reaction of 1,3-diketones with N-CBz imines, the products were isolated in up to 61% ee, while in the reaction with diethyl malonate enantioselectivities up to 71% were reached.

Squaric acid-based peptidic inhibitors of matrix metalloprotease-1

Onaran, M. Burak,Comeau, Anthony B.,Seto, Christopher T.

, p. 10792 - 10802 (2007/10/03)

A series of squaric acid-peptide conjugates were synthesized and evaluated as inhibitors of MMP-1. The cyclobut-3-enedione core was substituted at the 3-position with several functional groups, such as -N(alkyl)OH, -NHOH, and -OH, that are designed to bind to the zinc atom in the active site of the metalloprotease. The 4-position of the cyclobut-3-enedione was derivatized with mono- or dipeptides that are designed to bind in the S1′ and S2′ subsites of the enzyme, and position the metal chelating group appropriately in the active site for binding to zinc. Positional scanning revealed that -N(Me)OH provided the highest level of inhibition among the chelating groups that were tested, and Leu-Tle-NHMe was the preferred amino acid sequence. A combination of these groups yielded an inhibitor with an IC50 value of 95 μM. For one inhibitor, conversion of one of the carbonyl groups on the cyclobut-3-enedione core to a thiocarbonyl group resulted in a 18-fold increase in potency, and yielded a compound with an IC50 value of 15 μM.

Process for the preparation of N-carboxy-t-leucine anhydride

-

, (2008/06/13)

Process for the preparation of N-carboxy-t-leucine anhydride in which the corresponding N-carboxy-t-leucine is subjected to a cyclization with the aid of an acyl halogenide. Preferably, acetyl chloride is used as acyl halogenide. The N-carboxy-t-leucine anhydride obtained optionally is subsequently converted into a t-leucine-N-substituted amide with the aid of the corresponding amine. Preferably, methyl amine is chosen as the amine, and the reaction is carried out in a mixture of water and methanol as solvent.

Rapid optimization of the hydrolysis of N-trifluoroacetyl-S-tert-leucine-N-methylamide using high-throughput chemical development techniques

Rosso, Victor W.,Pazdan, James L.,Venit, John J.

, p. 294 - 298 (2013/09/07)

Our efforts are focused on the application of automation to Process R&D. This article will describe the application of high throughput methods to rapidly investigate a development challenge. In this case we needed to study the deprotection of N-trifluoroacetyl-S-tert-leucine-N-methylamide which afforded a lower than expected yield when subjected to standard deprotection reaction conditions. This chemistry was systematically investigated by a sequential series of high-throughput experiments using various automated and semi-automated systems. The studies included a combinatorial screen of discrete reaction conditions, a screening DOE to study a broad range of continuous factors, and a two-factor central composite design to optimize the important factors. By applying high-throughput methods we were able to optimize the yield of the reaction by performing a large number of experiments in a short period of time.

FORMAMIDES AS THERAPEUTIC AGENTS

-

, (2008/06/13)

A family of compounds having the general structural formula where W is a reverse hydroxamic acid group, and R 1, R 2, R 3, R 4, R 5 and R 6 are as described in the specification, or a pharmaceutically acceptable salt, solvate, biohydrolyzable ester, biohy

Metalloproteinase inhibitors, pharmaceutical compositions containing them, and their use

-

, (2008/06/13)

The present invention is directed to compound of the formula I: STR1 wherein R1, R2, R3, R4, R5, X, Y, and STR2 are as defined herein. These compounds are useful for inhibiting the activity of a metalloproteinase by contacting the metalloproteinase with an effective amount of the inventive compounds.

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