162458-72-2

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 162458-71-1 methyl (2R)-2-amino-2-(3-bromo-4-hydroxyphenyl)acetate 
• 37763-23-8 D-2-p-hydroxyphenylglycine methyl ester 
• 139517-61-6 (R)-3-bromo-4-hydroxyphenylglycine 
• 22818-40-2 D-4-hydroxyphenylglycine 

Downstream Products

• 139517-62-7 (2R)-2-(3-bromo-4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid 
• 229154-35-2 4-{4-[3-benzyloxy-1-benzyloxymethyl-2-(tert-butyl-dimethyl-silanyloxy)-propoxy]-3-bromo-phenyl}-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 229154-37-4 (R)-4-[4-((1R,2S)-3-Benzyloxy-1-benzyloxymethyl-2-hydroxy-propoxy)-3-bromo-phenyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 162458-73-3 (R)-4-(3-Bromo-4-hydroxy-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 162458-74-4 (R)-4-(3-Bromo-4-methoxy-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 162458-76-6 [(R)-1-(3-Bromo-4-hydroxy-phenyl)-2-hydroxy-ethyl]-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Identification and Profiling of a Novel Diazaspiro[3.4]octane Chemical Series Active against Multiple Stages of the Human Malaria Parasite Plasmodium falciparum and Optimization Efforts

A novel diazaspiro[3.4]octane series was identified from a Plasmodium falciparum whole-cell high-throughput screening campaign. Hits displayed activity against multiple stages of the parasite lifecycle, which together with a novel sp3-rich scaffold provided an attractive starting point for a hit-to-lead medicinal chemistry optimization and biological profiling program. Structure-activity-relationship studies led to the identification of compounds that showed low nanomolar asexual blood-stage activity (50 nM) together with strong gametocyte sterilizing properties that translated to transmission-blocking activity in the standard membrane feeding assay. Mechanistic studies through resistance selection with one of the analogues followed by whole-genome sequencing implicated the P. falciparum cyclic amine resistance locus in the mode of resistance.

Synthesis of orthogonally protected actinoidic acid trimethyl ether

- We describe the asymmetric synthesis of actinoidic acid trimethyl ether with orthogonal protecting groups on the respective amino and carboxyl groups. The Stille biaryl coupling reaction of suitably functionalized aryl bromide and (trimethylstannyl)benz

An intramolecular, Ni(0)-mediated approach to the nonracemic biaryl portion of vancomycin

Using a tether derived from tartaric acid to which is attached two halogenated phenylglycine residues, a Ni(0)-induced biaryl coupling can be effected with complete control of axial chirality.

A concise route to biaryls: Formal synthesis of biaryl diamino diacid (AB segment) of vancomycin

An efficient approach to the AB segment of vancomycin involving triphenylphosphine-catalysed coupling of the substituted aryl lithio compound (13) with palladium complex (14) of aromatic Schiff base derived from 3,5- dimethoxybenzaldehyde is described.