166383-82-0

Upstream product

• 174541-87-8 (2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-5-<(β-naphthyl)sulphonyloxy>-3-pentanol 
• 174541-86-7 (2R,3R)-1-benzyloxy-2-(tert-butoxycarbonyl)amino-3,5-pentandiol 
• 174541-85-6 (4R,5R)-4-Benzyloxymethyl-5-(2-chloro-ethyl)-oxazolidin-2-one 
• 153805-41-5 methyl (4R,5R)-4-(benzyloxy)methyl-2-oxo-5-oxazolidineacetate 
• 153805-45-9 (4R,5R)-4-(benzyloxy)methyl-5-(2-hydroxyethyl)-2-oxo-oxazolidine 
• 166383-69-3 (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 166383-69-3 (2R,3R)-1-t-Butoxycarbonyl-2-benzyloxymethyl-3-hydroxypyrrolidine 
• 567-35-1 (2S,3R)-3-hydroxyproline 

Relevant academic research and scientific papers

Chiral 4,5-Disubstituted Oxazolidin-2-ones: Stereoselective Synthesis of β-Hydroxy-α-amino Acids

The stereocontrolled synthesis of β-hydroxy-α-amino acids from O-benzyl D- and L-serine, by the use of 4,5-disubstituted oxazolidin-2-ones as chiral intermediates, is presented as a suitable alternative to the known procedures.The reported synthesis of both enantiomers of threo-3-hydroxyglutamic acid and (2S,3R)-3-hydroxyproline together with a flexible and stereodivergent preparation of threonine analogues is discussed as an example of the versatility of the present approach.

A straightforward synthesis of (2S,3R)-3-hydroxyproline and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine

A stereocontrolled synthesis of (2S,3R)-3-hydroxyproline 1, and trans-(2R,3S)-2-hydroxymethyl-3-hydroxypyrrolidine 2 has been achieved in 21% and 38% yield via the homochiral 4,5-disubstituted oxazolidin-2-one 3. The trans relationship in 2 has been introduced by a modified Mitsunobu reaction.