152857-79-9

Upstream product

• 108-22-5 Isopropenyl acetate 
• 93723-61-6 1-(N,N-dibenzyl)amino-2-propanol 
• 2799-17-9 (S)-1-amino-2-propanol 
• 100-52-7 benzaldehyde 
• 60479-65-4 (S)-2-(N,N-dibenzylamino)-1-propanol 
• 143746-16-1 2,2,4,4-Tetramethyl-oxazolidine-3-carboxylic acid (S)-2-dibenzylamino-1-methyl-ethyl ester 

Relevant academic research and scientific papers

Discovery of a Novel Series of Potent and Selective Alkynylthiazole-Derived PI3KγInhibitors

Phosphoinositide 3-kinases (PI3Ks) are a family of enzymes that control a wide variety of cellular functions such as cell growth, proliferation, differentiation, motility, survival, and intracellular trafficking. PI3Kγplays a critical role in mediating leukocyte chemotaxis as well as mast cell degranulation, making it a potentially interesting target for autoimmune and inflammatory diseases. We previously disclosed a novel series of PI3Kγinhibitors derived from a benzothiazole core. The truncation of the benzothiazole core led to the discovery of a structurally diverse alkynyl thiazole series which displayed high PI3Kγpotency and subtype selectivity. Further medicinal chemistry optimization of the alkynyl thiazole series led to identification of compounds such as 14 and 32, highly potent, subtype selective, and CNS penetrant PI3Kγinhibitors. Compound 14 showed robust inhibition of PI3Kγmediated neutrophil migration in vivo.

Synthetic and theoretical investigation on the one-pot halogenation of β-amino alcohols and nucleophilic ring opening of aziridinium ions

Aziridinium ions are useful reactive intermediates for the synthesis of enantiomerically enriched building blocks. However, N,N-dialkyl aziridinium ions are relatively underutilized in the synthesis of optically active molecules as compared to other three

SYNTHESIS OF THERAPEUTIC AND DIAGNOSTIC DRUGS CENTERED ON REGIOSELECTIVE AND STEREOSELECTIVE RING OPENING OF AZIRIDINIUM IONS

Stereoselective and regioselective synthesis of compounds via nucleophilic ring opening reactions of aziridinium ions for use in stereoselective and regioselective synthesis of therapeutic and diagnostic compounds.

Combined ruthenium(II) and lipase catalysis for efficient dynamic kinetic resolution of secondary alcohols. Insight into the racemization mechanism

Pentaphenylcyclopentadienyl ruthenium complexes (3) are excellent catalysts for the racemization of secondary alcohols at ambient temperature. The combination of this process with enzymatic resolution of the alcohols results in a highly efficient synthesis of enantiomerically pure acetates at room temperature with short reaction times for most substrates. This new reaction was applied to a wide range of functionalized alcohols including heteroaromatic alcohols, and for many of the latter, enantiopure acetates were efficiently prepared for the first time via dynamic kinetic resolution (DKR). Different substituted cyclopentadienyl ruthenium complexes were prepared and studied as catalysts for racemization of alcohols. Pentaaryl-substituted cyclopentadienyl complexes were found to be highly efficient catalysts for the racemization. Substitution of one of the aryl groups by an alkyl group considerably slows down the racemization process. A study of the racemization of (S)-1-phenylethanol catalyzed by ruthenium hydride η5-Ph5CpRu(CO) 2H (8) indicates that the racemization takes place within the coordination sphere of the ruthenium catalyst. This conclusion was supported by the lack of ketone exchange in the racemization of (S)-1-phenylethanol performed in the presence of p-tolyl methyl ketone (1 equiv), which gave 1% of 1-(p-tolyl)ethanol. The structures of ruthenium chloride and iodide complexes 3a and 3c and of ruthenium hydride complex 8 were confirmed by X-ray analysis.

Stereoselective deprotonation of chiral and achiral 2-aminoalkyl carbamates: Synthesis of optically active β-amino alcohols via 1-oxy- substituted alkyllithium intermediates

A facile protocol for the electrophilic C-substitution (methylation, acylation, α-hydroxyalkylation, and carboxylation) of several 2-(N,N- dibenzylamino)alkan-1-ols via the carbamates 10 is reported. The stereochemistry of the lithiation is greatly influenced by the complexing diamine. The substrate-directed selection between the diastereotopic a-pro-R and pro-S protons in the TMEDA-assisted deprotonation is largely shifted towards pro-S-selectivity in the presence of (-)-sparteine (4). Each of both diastereomeric series is readily accessible in several cases.

Preparation of sec. or tert. alcohols

A process for the preparation of a compound of the formula STR1 which comprises deprotonating a carbamate of the formula STR2 in an inert solvent with a selective base, in the presence of a chelate-forming diamine to give a compound of the formula STR3 and then reacting III in an inert solvent, either with an achiral electrophile of the formula (IV) or (V) or with an optionally prochiral electrophile of the formula (VI) STR4 and in the case in which R1 represents an electrofugic leaving group, optionally again electrophilically substituted with the formation of an acyl anion and renewed deprotonation, and in a last step, solvolytically removing the protecting group --CO--NR10 R11.

Optically active α-amino aldehydes, process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active β-amino alcohols

The invention relates to new optically active α-amino aldehydes of the formulae STR1 in which R1 represents an optionally substituted alkyl, alkenyl, aralkyl or aryl radical, and R2 and R3, independently of one another, denote an optionally substituted alkyl, alkenyl, cycloalkyl or aralkyl group, together form an optionally substituted phenylene-(1,2)-bis-methylene radical, or R2 is an optionally substituted, alkyl, cycloalkyl or aralkyl radical, and R3 forms together with R1 a 1,3-propylene radical. a process for the preparation thereof, and the use thereof for the stereoselective preparation of optically active β-amino alcohols.