84500-43-6

Basic information

• Product Name: (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester
• Synonyms: (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester
• CAS NO: 84500-43-6
• Molecular Weight: 371.433
• Mol File: 84500-43-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester(84500-43-6)
• EPA Substance Registry System: (2S,3S)-N-(benzyloxycarbonyl)-3-hydroxyleucine benzyl ester(84500-43-6)

Safety Data

• Hazardous Substances Data: 84500-43-6(Hazardous Substances Data)

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 
• 1647153-59-0 benzyl (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylate 
• 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 

Downstream Products

• 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 

Relevant articles and documents

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.