128053-01-0

Basic information

• Product Name: (2S,3S)-N-benzyl-3-hydroxyleucine
• Synonyms: (2S,3S)-N-benzyl-3-hydroxyleucine
• CAS NO: 128053-01-0
• Molecular Weight: 237.299
• Mol File: 128053-01-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: (2S,3S)-N-benzyl-3-hydroxyleucine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-N-benzyl-3-hydroxyleucine(128053-01-0)
• EPA Substance Registry System: (2S,3S)-N-benzyl-3-hydroxyleucine(128053-01-0)

Safety Data

• Hazardous Substances Data: 128053-01-0(Hazardous Substances Data)

Upstream product

• 69143-05-1 (E)-4-methyl-pent-2-en-1-ol 
• 1775-44-6 (2E)-4-methylpent-2-enoic acid 
• 100-46-9 benzylamine 
• 145822-80-6 t-Butyl (2S,3S)-(-)-2-bromo-3-hydroxy-4-methylpentanoate 
• 145919-92-2 (2R,3S)-3-Isopropyl-oxirane-2-carboxylic acid tert-butyl ester 
• 151302-40-8 (4R,5S)-3-Benzyl-4-hydroxymethyl-5-isopropyl-oxazolidin-2-one 
• 3173-56-6 benzyl isothiocyanate 
• 89459-98-3 (2S,3S)-2,3-epoxy-4-methyl-1-pentanol 
• 128053-00-9 (2R,3S)-2,3-epoxy-4-methylpentanoic acid 
• 151302-41-9 (4S,5S)-3-Benzyl-5-isopropyl-2-oxo-oxazolidine-4-carboxylic acid 

Downstream Products

• 5817-22-1 (2RS,3RS)-2-amino-3-hydroxy-4-methylpentanoic acid 
• 10148-70-6 (2S,3S)-3-hydroxyleucine 

Relevant articles and documents

Total synthesis of (+)-lactacystin

A total synthesis of the novel neurotrophic agent (+)-lactacystin (1) has been achieved in 11 steps and 14% overall yield from (2R,3S)-3-hydroxyleucine [(+)-16]. The construction and bioassay of several active analogs are also described. A new asymmetric approach furnished the four stereoisomers of 3-hydroxyleucine, as required starting materials in high overall yield and enantiomeric purity.

An enantioselective synthesis of (2S,3S)- and (2R,3S)-3-hydroxyleucine

α-Bromo β-hydroxy ester 2 was prepared in a preparative scale by a 96 : 4 enantioselective aldol reaction of t-butyl bromoacetate with isobutyraldehyde and converted efficiently to either (2S,3S)-or (2R,3S)-3-hydroxyleucine (7 or 11).