1461641-97-3

Usage

Uses

Used in Organic Synthesis:
(2S,3R)-2-((S)-1,1-dimethylethylsulfinamido)-3-methylpent-4-enoic acid is used as a building block in organic synthesis for the creation of more complex molecules. Its unique structure and functional groups allow for versatile reactions and the formation of a wide range of compounds.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, (2S,3R)-2-((S)-1,1-dimethylethylsulfinamido)-3-methylpent-4-enoic acid is used as a potential pharmaceutical candidate. Its specific stereochemistry and functional groups may contribute to the development of new drugs with unique mechanisms of action.
Used in Biochemistry Research:
(2S,3R)-2-((S)-1,1-dimethylethylsulfinamido)-3-methylpent-4-enoic acid is used as a research tool in biochemistry to study enzyme mechanisms, protein interactions, and other biological processes. Its unique structure allows for the investigation of various biochemical phenomena.
The precise properties and potential uses of (2S,3R)-2-((S)-1,1-dimethylethylsulfinamido)-3-methylpent-4-enoic acid would likely be determined through further chemical and biological study, as its complex nature and diverse functional groups offer a wide range of possibilities for applications across different industries.

Upstream product

• 99687-39-5 (E)-but-2-en-1-ylboronic acid 
• 69611-02-5 (E)-2-(but-2-enyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 298-12-4 Glyoxilic acid 
• 343338-28-3 (S)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

Diastereoselective amidoallylation of glyoxylic acid with chiral tert-butanesulfinamide and allylboronic acid pinacol esters: Efficient synthesis of optically active γ,δ-unsaturated α-amino acids This work is dedicated to Dr. Masanori Sakamoto, Professor Emeritus of Meiji Pharmaceutical University, on the occasion of his 77th birthday (KIJU)

A convenient synthesis of δ,γ-unsaturated amino acids has been developed. After a mixture of (R)-tert-butanesulfinamide and glyoxylic acid with molecular sieves in CH2Cl2 was stirred for 42 h at room temperature, allylboronic acid pinacol ester was added to the mixture to give (R)-2-((R)-tert-butanesulfinamido)pent-4-enoic acid with high diastereoselectivity. The corresponding reaction of (Z)-crotylboronic acid pinacol ester produced no product; however, that of (E)-crotylboronic acid pinacol ester produced (2R,3S)-2-((R)-tert-butylsulfinamido)-3-methylpent-4- enoic acid with excellent diastereoselectivity.

Discovery of an Orally Available Diazabicyclooctane Inhibitor (ETX0282) of Class A, C, and D Serine β-Lactamases

Multidrug resistant Gram-negative bacterial infections are an increasing public health threat due to rapidly rising resistance toward β-lactam antibiotics. The hydrolytic enzymes called β-lactamases are responsible for a large proportion of the resistance phenotype. β-Lactamase inhibitors (BLIs) can be administered in combination with β-lactam antibiotics to negate the action of the β-lactamases, thereby restoring activity of the β-lactam. Newly developed BLIs offer some advantage over older BLIs in terms of enzymatic spectrum but are limited to the intravenous route of administration. Reported here is a novel, orally bioavailable diazabicyclooctane (DBO) β-lactamase inhibitor. This new DBO, ETX1317, contains an endocyclic carbon-carbon double bond and a fluoroacetate activating group and exhibits broad spectrum activity against class A, C, and D serine β-lactamases. The ester prodrug of ETX1317, ETX0282, is orally bioavailable and, in combination with cefpodoxime proxetil, is currently in development as an oral therapy for multidrug resistant and carbapenem-resistant Enterobacterales infections.

BETA-LACTAMASE INHIBITOR COMPOUNDS

The present invention is directed to compounds which are beta-lactamase inhibitors. The compounds and their pharmaceutically acceptable salts are useful in combination with beta- lactam antibiotics, for the treatment of bacterial infections, including infections caused by drug resistant organisms, including multi-drug resistant organisms. The present invention includes compounds according to Formula (I): or a pharmaceutically acceptable salt thereof, wherein the values of R1, R2, R3, R4, R5 and R6 are described herein.