208709-17-5

Upstream product

• 922524-49-0 4-[3-(4-benzyl-2-oxo-oxazolidin-3-yl)-1-hydroxy-2-methyl-3-oxo-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 98-88-4 benzoyl chloride 
• 208711-86-8 (2R,3S)-2-(1-Ethoxy-ethoxymethyl)-3,5-dihydroxy-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 922524-58-1 4-[1-benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 922524-57-0 4-[3-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-2-methyl-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 922524-59-2 4-(1-benzyloxy-3-hydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 922524-54-7 4-(1,3-dihydroxy-2-methyl-propyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 121964-38-3 3-benzyloxy-2-hydroxymethyl-4-methyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 208709-15-3 (2R,3S,4S)-1-tert-butoxycarbonyl-3-benzoyloxy-2-hydroxymethyl-4-methylpyrrolidine 
• 276697-21-3 (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl,N-oxy)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine 
• 276697-19-9 (2R,3S,4S)-2-acetoxymethyl-4-(N,N-dimethyl)aminomethyl-3-benzoyloxy-1-tert-butoxycarbonylpyrrolidine 
• 276697-23-5 (2R,3S)-2-acetoxymethyl-3-benzoyloxy-1-tert-butoxycarbonyl-4-exo-methylenepyrrolidine 
• 276697-25-7 (2R,3S)-3-benzoyloxy-1-tert-butoxycarbonyl-2-hydroxymethyl-4-exo-methylenepyrrolidine 
• 922524-55-8 4-[1-benzyloxy-2-methyl-3-(toluene-4-sulfonyloxy)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 

Relevant academic research and scientific papers

General strategy for a short and efficient synthesis of 3-hydroxy-4-methylprolines (HMP)

The non-proteinogenic amino acid 3-hydroxy-4-methylproline (HMP) is an active constituent of some potent antimicrobials including echinocandins, nostopeptins, pneumocandins, sporiofungin and mulundocandins. A synthesis has been achieved in 10 steps with 2

Diastereoselective synthesis of (2S,3S,4S)-3-hydroxy-4-methylproline, a common constituent of several antifungal cyclopeptides

(2S,3S,4S)-3-Hydroxy-4-methylproline 2 was synthesized from unsaturated γ-lactams 4 and 5 derived from (S)-pyroglutaminol. Starting from 5, haplophilic effect in the hydrogenation of a 4-exo-methylenic intermediate improved the diastereoselectivity of the synthesis, which was achieved in 19% yield. (C) 2000 Elsevier Science Ltd.

Synthesis of the nonproteinogenic amino acid (2s,3s,4s)-3-hydroxy-4- methylproline, a constituent of echinocandins

An enantioselective synthesis of the unusual 3,4-disubstituted proline 2, a constituent of antifungal echinocandins, has been achieved through 1,3- dipolar cycloaddition of N-methylnitrone to the α,β-unsaturated lactam 4 derived from (S)-pyroglutaminol.