157183-67-0

Usage

InChI:InChI=1/C21H39NO5/c1-2-3-4-11-14-18(24)15-12-9-7-5-6-8-10-13-16-19(25)21(22,17-23)20(26)27/h8,10,19,23,25H,2-7,9,11-17,22H2,1H3,(H,26,27)/b10-8+/t19-,21-/m0/s1

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 
• 78009-99-1 7-(2-n-hexyl-1,3-dioxolan-2-yl)-n-heptyl-triphenylphosphonium bromide 
• 270086-15-2 methyl (2S,3R)-2-acetamido-6-benzyloxy-3-hydroxyhexanoate 
• 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 
• 176703-36-9 methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-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 
• 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 
• 1055036-36-6 (4S,5S)-5-(3-Benzyloxy-propyl)-4-hydroxymethyl-2-phenyl-4,5-dihydro-oxazole-4-carboxylic acid methyl ester 
• 270086-11-8 methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate 

Relevant academic research and scientific papers

Total synthesis of myriocin and mycestericin D employing Rh(II)-catalyzed C[sbnd]H amination followed by stereoselective alkylation

Total synthesis of myriocin and mycestericin D was achieved using the Du Bois Rh(II)-catalyzed C[sbnd]H amination of a sulfamate and subsequent alkylation as a key step. The reaction of a sulfamate with PhI(OAc)2and MgO in the presence of Rh2(OAc)4gave oxathiazinane N,O-acetal as the sole product in high yield. Alkylation of N,O-acetal using vinylmagnesium bromide in the presence of ZnCl2proceeded stereoselectively to provide an oxathiazinane bearing a quaternary chiral center in high yield. Myriocin and mycestericin D were synthesized from a common synthetic intermediate. This route includes the first application of the Du Bois procedure for constructing a quaternary chiral center.

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.