194031-58-8

Upstream product

• 1775-44-6 (2E)-4-methylpent-2-enoic acid 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 3282-30-2 pivaloyl chloride 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 

Downstream Products

• 176018-92-1 (R)-3-((R)-4-Methyl-3-phenyl-pentanoyl)-4-phenyl-oxazolidin-2-one 
• 1208099-21-1 C₄₂H₅₄BrN₃O₁₁ 
• 1208099-22-2 C₄₂H₅₄N₆O₁₁ 
• 198014-55-0 3(2'R,3'R),4(R)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone 
• 198014-59-4 3(2'S,3'R),4(R)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone 
• 198014-51-6 3(2'R,3'R),4(R)-3-[2'-bromo-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone 
• 198014-99-2 (2R,3R)-2-azido-3-(4'-methoxyphenyl)-4-methylpentanoic acid 

Relevant academic research and scientific papers

Synthetic studies of cyclic peptides stephanotic acid methyl ester, celogentin C, and moroidin

An account of the total synthesis of stephanotic acid methyl ester and celogentin C is presented. The present synthesis features a tandem asymmetric Michael addition/bromination sequence for the synthesis of leucine-tryptophan moiety, and an oxidative coupling reaction to form the tryptophan-imidazole linkage. Moreover, the total synthesis of moroidin had also been studied, and three different synthetic strategies for the construction of the right-hand ring of moroidin were studied.

Stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C

(Figure Presented) A highly stereocontrolled and efficient total synthesis of (-)-stephanotlc acid methyl ester and (-)-celogentin C was accomplished In longest linear 14 steps (4.6% overall yield) and In 20 steps (1.6% overall yield) from L-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.

Structure-activity relationships of pregabalin and analogues that target the α2-δ protein

Pregabalin exhibits robust activity in preclinical assays indicative of potential antiepileptic, anxiolytic, and antihyperalgesic clinical efficacy. It binds with high affinity to the α2-δ subunit of voltage-gated calcium channels and is a substrate of the system L neutral amino acid transporter. A series of pregabalin analogues were prepared and evaluated for their α2-δ binding affinity as demonstrated by their ability to inhibit binding of [3H]gabapentin to pig brain membranes and for their potency to inhibit the uptake of [3H]leucine into CHO cells, a measure of their ability to compete with the endogenous substrate at the system L transporter. Compounds were also assessed in vivo for their ability to promote anxiolytic, analgesic, and anticonvulsant actions. These studies suggest that distinct structure activity relationships exist for α2-δ binding and system L transport inhibition. However, both interactions appear to play an important role in the in vivo profile of these compounds.

Synthesis and conformational features of topographically constrained designer chimeric amino adds: The β-isopropyl phenylalanines

All four optically pure isomers of the highly conformationally constrained novel chimeric amino acid, β-isopropylphenylalanine or β- phenylleucine, were asymmetrically synthesized in five to six steps in 20 - 25% overall yield. Computer-assisted molecular modeling revealed that the β- isopropyl group in these chimeric amino acids plays the dominant role in determining the most favorable side chain conformations.

Asymmetric synthesis of all four isomers of topographically constrained novel amino acids: β-isopropyltyrosines

All four stereoisomers of the highly constrained novel amino acid, β-isopropyltyrosine, have been synthesized with high stereoselectivities (>90% de) and in 40-50% overall yields by using the optically pure 4-phenyloxazolidinone as a chiral auxiliary via asymmetric Michael addition, direct or indirect azidation, hydrogenolysis and demethylation reactions.

Total asymmetric synthesis of highly constrained amino acids β-isopropyl-2',6'-dimethyl-tyrosines

All four stereoisomers of the highly constrained aromatic α-amino acid β-isopropyl-2',6'-dimethyltyrosine have been asymmetrically synthesis on a large scale. A catalytic asymmetric Michael addition of an organocuprate to a chiral α,β-unsaturated acyloxazolidinone and subsequent direct or indirect stereoselective electrophilic azidation of the α-position of the resulting product was followed by hydrolysis, hydrogenation and finally deprotection of the phenol group to afford the desired amino acids. The reactions generally proceeded in good stereoselectivities (75-95% ee/de) and yields (70-90%), making these optically pure amino acids available in large scale practical for the synthesis of peptides and other studies.