150744-82-4

Upstream product

• 1033441-80-3 C₂₁H₂₃NO₄ 
• 124782-04-3 methyl (2S,3R)-3--2-hydroxy-4-phenylbutanoate 
• 137028-93-4 (4R,5S)-4-benzyl-3-benzyloxycarbonyl-2,2-dimethyl-oxazolidine-5-carboxylic acid methyl ester 

Downstream Products

• 137028-93-4 (4R,5S)-4-benzyl-3-benzyloxycarbonyl-2,2-dimethyl-oxazolidine-5-carboxylic acid methyl ester 
• 137028-96-7 (4'R,5'S)-4-(4'-benzyl-3'-benzyloxycarbonyl-2',2'-dimethyl-oxazolidine-5'-yl)-2-isobutyl-2-methoxycarbonyl-4-oxobutyric acid methyl ester 
• 137028-95-6 (4'R,5'S)-4-(4'-benzyl-3'-benzyloxycarbonyl-2',2'-dimethyl-oxazolidine-5'-yl)-2-methoxycarbonyl-4-oxobutanoic acid methyl ester 
• 137028-94-5 (4R,5S)-4-benzyl-3-benzyloxycarbonyl-5-(chloromethyl)carbonyl-2,2-dimethyl-oxazolidine 

Relevant academic research and scientific papers

Stereoselective synthesis of α-hydroxy-β-amino acid derivatives from β-hydroxy-γ,δ-unsaturated sulfilimine

The first report on the use of N-sulfinyl benzylcarbamate for the preparation of N-Cbz sulfilimine from the corresponding sulfoxide is reported. The sulfilimine moiety is utilized as an intramolecular nucleophile for the regio- and stereoselective heterofunctionalization of an alkene to furnish a bromo carbamate which is used as a key advanced intermediate in the synthesis of representative α-hydroxy-β-amino acid derivatives.

Ketomethylenebestatin: Synthesis and aminopeptidase inhibition

The synthesis of (6R,5S,2RS)-6-amino-5-hydroxy-2-isobutyl-4-oxo-7-phenylheptanoic acid (9), a carbaanalogue of the aminopeptidase (AP) inhibitor bestatin (1) is described. This synthesis was carried out by a malonic ester alkylation with the suitably protected halomethyl ketone of (2S,3R)-AHPBA, followed by a second alkylation with isobutyl bromide of the resulting 4-ketodiester, and subsequent decarboxylation and deprotection. The inhibitory potencies of the 1:1 diastereomeric mixture 9 against AP-B, AP-M and Leu-AP were approximately 10-fold lower than those of bestatin.