1647153-72-7

Upstream product

• 188802-11-1 (2R,3S)-2-Amino-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-3-ol 
• 188802-09-7 (2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol 
• 100-39-0 benzyl bromide 
• 1647153-71-6 benzyl (4S,5S)-N-(tert-butyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylate 
• 1449475-66-4 (4S,5S)-N-(tert-butyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid 
• 1647153-49-8 (4R,5S)-N-(tert-butyloxycarbonyl)-4-hydroxymethyl-5-isopropyl-2,2-dimethyl-oxazolidine 
• 1647153-48-7 (4R,5S)-N-(tert-butyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-47-6 (2R,3S)-2-(tert-butyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methyl-pentane-1,3-diol 

Relevant academic research and scientific papers

Amino acid motifs in natural products: Synthesis of O-acylated derivatives of (2S,3S)-3-hydroxyleucine

(2S,3S)-3-Hydroxyleucine can be found in an increasing number of bioactive natural products. Within the context of our work regarding the total synthesis of muraymycin nucleoside antibiotics, we have developed a synthetic approach towards (2S,3S)-3- hydroxyleucine building blocks. Application of different protecting group patterns led to building blocks suitable for C- or N-terminal derivatization as well as for solid-phase peptide synthesis. With respect to according motifs occurring in natural products, we have converted these building blocks into 3-O-acylated structures. Utilizing an esterification and cross-metathesis protocol, (2S,3S)-3-hydroxyleucine derivatives were synthesized, thus opening up an excellent approach for the synthesis of bioactive natural products and derivatives thereof for structure activity relationship (SAR) studies.