176703-36-9

Upstream product

• 168695-89-4 (2S,3S)-2-amino-6-(benzyloxy)-3-hydroxyhexanoic acid 
• 176703-35-8 (2S,3S)-2-Amino-6-benzyloxy-3-hydroxy-hexanoic acid methyl ester 
• 1055036-36-6 (4S,5S)-5-(3-Benzyloxy-propyl)-4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 270086-15-2 methyl (2S,3R)-2-acetamido-6-benzyloxy-3-hydroxyhexanoate 
• 7471-86-5 methyl benzimidate 
• 270086-13-0 (2S,3R)-2-amino-6-(benzyloxy)-3-hydroxyhexanoic acid 
• 176703-32-5 methyl (2S,3R)-2-benzamido-6-benzyloxy-3-hydroxyhexanoate 
• 176703-31-4 methyl (4S,5S)-5-(3-benzyloxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate 
• 176703-34-7 methyl (2S,3S)-2-acetamido-6-benzyloxy-3-hydroxyhexanoate 
• 189071-56-5 (2S,3SR)-2-amino-6-benzyloxy-3-hydroxyhexanoic acid 
• 93-97-0 benzoic acid anhydride 
• 270086-11-8 methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate 
• 176703-33-6 methyl (4S,5S)-4-acetoxymethyl-5-(3-benzyloxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate 

Downstream Products

• 157183-67-0 (2S,3S)-(E)-2-amino-3-hydroxy-2-hydroxymethyl-14-oxoicos-6-enoic acid 
• 176703-37-0 methyl (4S,5S)-4-acetoxymethyl-5-[(3E)-11,11-ethylenedioxyheptadec-3-enyl]-2-phenyl-Δ²-oxazoline-4-carboxylate 
• 270086-12-9 methyl (4S,5S)-4-acetoxymethyl-5-[(3Z)-11,11-ethylenedioxyheptadec-3-enyl]-2-phenyl-Δ²-oxazoline-4-carboxylate 

Relevant academic research and scientific papers

An asymmetric total synthesis of a potent immunosuppressant, mycestericins D and F, through an aldol reaction using L-threonine aldolase

L-Threonine aldolase from Candida humicola catalyzed the aldol reaction of 4-benzyloxybutanal (1) with glycine to give β-hydroxy-α-amino acids (2e,t), whose erythro / threo ratio was controlled by using either kinetic or thermodynamic conditions. The erythro derivative (4e) was effectively converted to mycestericins D and F via a stereoselective hydroxymethylation of oxazoline derivative (6) as the key step.

Kinetic and thermodynamic control of L-threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D

L-Threonine aldolase catalyzes the aldol condensation of γ-benzyloxybutanal and glycine with high erythro/threo selectivity under a kinetically controlled condition. The erythro product was used in the synthesis of mycestericin D, a potent immunosuppressant.