357617-22-2

Upstream product

• 357617-20-0 (4S,5R)-5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-oxooxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 357617-14-2 (4S)-4-benzyl-3-[(4S,5R)-1-[5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidin-4-yl]methanoyl]oxazolidin-2-one 
• 357617-18-6 (4S,5R)-5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-3,4-dicarboxylic acid 3-tert-butyl ester 4-methyl ester 
• 357617-16-4 (4S,5R)-5-[3,4-bis(benzyloxy)-2-fluorophenyl]-2-thioxooxazolidine-4-carboxylic acid methyl ester 
• 61338-96-3 3,4-bis(benzyloxy)-2-fluorobenzaldehyde 
• 24424-99-5 di-tert-butyl dicarbonate 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 357617-26-6 (2S,3R)-2-amino-3-[3,4-bis(benzyloxy)-2-fluorophenyl]-3-hydroxypropionic acid 

Relevant academic research and scientific papers

Synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine as potential in vivo precursors of fluorinated norepinephrines

The title compounds were prepared by the aldol condensation of 3,4-dibenzyloxy-2-fluorobenzaldehyde and 4,5-dibenzyloxy-2-fluorobenzaldehyde with the oxazolidinone 2, a chiral glycine equivalent. Removal of the chiral auxiliary and blocking groups produced the target amino acids 2-fluoro- and 6-fluoro-(2S,3R)-(3,4-dihydroxyphenyl)serine (1b and 1c) in >98% ee.

A convenient synthesis of 2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine using Sharpless asymmetric aminohydroxylation

Ring-fluorinated β-hydroxy α-amino methyl esters 3b,c were synthesized enantioselectively using Sharpless asymmetric aminohydroxylation. These were converted to 2-fluoro- and 6-fluoro-(2S,3R)-threo-(3,4-dihydroxyphenyl)serine 1b,c using our previously published procedure.