473709-99-8

Upstream product

• 1647153-54-5 (2R,3S)-2-(benzyloxycarbonylamino)-1-O-(tert-butyldimethylsilyl)-4-methylpentane-1,3-diol 
• 1647153-55-6 (4R,5S)-N-(benzyloxycarbonyl)-4-(tert-butyldimethylsilyloxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-56-7 (4R,5S)-N-(benzyloxycarbonyl)-4-(hydroxymethyl)-5-isopropyl-2,2-dimethyloxazolidine 
• 1647153-57-8 (4S,5S)-N-(benzyloxycarbonyl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid 
• 1647153-58-9 (4S,5S)-N²-(benzyloxycarbonyl)-N-(3',3'-diethoxypropan-1'-yl)-5-isopropyl-2,2-dimethyloxazolidine-4-carboxylic acid amide 
• 188802-09-7 (2R,3S)-1-(tert-Butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentan-3-ol 
• 188802-11-1 (2R,3S)-2-Amino-1-(tert-butyl-dimethyl-silanyloxy)-4-methyl-pentan-3-ol 

Downstream Products

• 473710-36-0 C₅₂H₈₃N₅O₁₃Si₂ 
• 473710-37-1 2-[3-(2-amino-3-hydroxy-4-methyl-pentanoylamino)-propylamino]-3-{3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-[3-(4-methoxy-benzyl)-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl]-tetrahydro-furan-2-yl}-3-hydroxy-propionic acid tert-butyl ester 

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.

Muraymycins, novel peptidoglycan biosynthesis inhibitors: Synthesis and SAR of their analogues

A series of Muraymycin analogues was synthesized. These analogues showed excellent antimicrobial activity against gram-positive organisms. These analogues also showed excellent inhibitory activity against the target peptidoglycan biosynthesis enzyme MraY,