188802-09-7

Upstream product

• 202478-34-0 (R)-methyl 2-(dibenzylamino)-3-hydroxypropanoate 
• 188802-06-4 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionic acid methyl ester 
• 100-39-0 benzyl bromide 
• 1068-55-9 isopropylmagnesium chloride 
• 188840-00-8 (R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-propionaldehyde 

Downstream Products

• 125473-34-9 (4S,5S)-5-Isopropyl-2-oxazolidinone-4-carboxylic acid 
• 1647153-68-1 (2S,3S)-O-((E)-non-2-enoyl)-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester 
• 1647153-67-0 (2S,3S)-O-acryloyl-N-(fluorenylmethyloxycarbonyl)-3-hydroxyleucine benzyl ester 
• 1647153-61-4 (2S,3S)-N-(benzyloxycarbonyl)-O-(6'-methylheptanoyl)-3-hydroxyleucine benzyl ester 
• 1647153-60-3 (2S,3S)-N-(benzyloxycarbonyl)-O-octanoyl-3-hydroxyleucine benzyl ester 
• 84500-43-6 (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester 
• 1647153-59-0 benzyl (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylate 
• 473709-99-8 (4S,5S)-N²-(benzyloxycarbonyl)-N-(3'-oxopropyl)-3-hydroxyleucine amide 
• 1647153-58-9 (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide 
• 1647153-57-8 (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid 
• 1647153-56-7 (4R,5S)-N-(benzyloxycarbonyl)-4-(hydroxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-55-6 (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-54-5 (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol 
• 1647153-72-7 C₄₂H₆₂N₆O₁₀S 

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.

A highly stereoselective synthesis of (2S,3S)-β-hydroxyleucine

A highly diastereoselective nucleophilic addition of Grignard reagent to N,N-dibenzyl-O-TBS-serinal 3 was the key step in the present synthesis of (2S,3S)-β-hydroxyleucine 1.