121695-09-8

Basic information

• Product Name: (2S,3S)-(-)-2-(2,4-dinitrophenyl)-3-hydroxyleucine
• Synonyms: (2S,3S)-(-)-2-(2,4-dinitrophenyl)-3-hydroxyleucine
• CAS NO: 121695-09-8
• Molecular Weight: 313.267
• Mol File: 121695-09-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3S)-(-)-2-(2,4-dinitrophenyl)-3-hydroxyleucine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-(-)-2-(2,4-dinitrophenyl)-3-hydroxyleucine(121695-09-8)
• EPA Substance Registry System: (2S,3S)-(-)-2-(2,4-dinitrophenyl)-3-hydroxyleucine(121695-09-8)

Safety Data

• Hazardous Substances Data: 121695-09-8(Hazardous Substances Data)

Upstream product

• 159718-19-1 (2R,3S)-(-)-ethyl 2,3-dihydroxy-3-propionate 2,3-cyclic sulphate 
• 159990-08-6 (2S,3S)-(-)-ethyl 2-azido-3-isopropyl-3-hydroxypropionate 
• 159718-20-4 (2S,3S)-(-)-2-azido-3-isopropyl-3-hydroxypropionic acid 
• 108666-30-4 (2R,3S)-(-)-ethyl 2,3-dihydroxy-3-propionate 
• 15790-86-0 ethyl-4-methyl-2-(E)-penteneoate 

Relevant articles and documents

A practical new asymmetric synthesis of (2S,3S)- and (2R,3R)-3-hydroxyleucine

A convenient new asymmetric synthesis of both enantiomers of erythro-3-hydroxyleucine is described. The key steps involve Sharpless asymmetric dihydroxylation (AD) of α,β-unsaturated ester 3, cyclic sulphate formation from the resulting diol, S(N)2 reaction with sodium azide, deesterification with aqueous sodium hydroxide, and hydrogenolysis. Utilising this route, (2S,3S)-(+)-3-hydroxyleucine (1) was obtained in 97% ee and 67% overall yield; the (2R,3R)-(-)-enantiomer was isolated in 92% ee and 57% overall yield.