(4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide

Base Information

• Chemical Name: (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide
• CAS No.: 332080-21-4
• Molecular Formula: C₁₃H₁₅NO₆
• Molecular Weight: 281.265
• Mol file: 332080-21-4.mol

Synonyms:(4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide

Chemical Property of (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide

There total 3 articles about (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

nitroacetic acid ethyl ester (626-35-7) + (2R,3S)-3-phenyloxirane-2-carbaldehyde (126720-47-6) → (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide (332080-21-4) + (4R,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide (332080-22-5)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃;

DOI:10.1021/ol0070379

Reference yield:

nitroacetic acid ethyl ester (626-35-7) + (2S,3S)-2,3-epoxy-3-phenyl-1-propanol (104196-23-8) → (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide (332080-21-4) + (4R,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide (332080-22-5)

Guidance literature:

With 1H-imidazole; 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene; In 1,2-dichloro-ethane; at 20 ℃;

DOI:10.1021/ol0070379

Reference yield:

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol (104196-23-8) → (4S,5S)-3-ethoxycarbonyl-4-hydroxy-5-[(S)-hydroxyphenylmethyl]-4,5-dihydroisoxazole 2-oxide (332080-21-4)

Guidance literature:

Multi-step reaction with 2 steps

1: bisacetoxyiodobenzene; tetramethylpiperidinyloxy radical / CH₂Cl₂ / 5 h / 20 °C

2: imidazole / CH₂Cl₂ / 20 °C

With 1H-imidazole; [bis(acetoxy)iodo]benzene; tetramethylpiperidinyloxy radical; In dichloromethane;

DOI:10.1021/ol0070379

upstream raw materials:

nitroacetic acid ethyl ester

(2R,3S)-3-phenyloxirane-2-carbaldehyde

(2S,3S)-2,3-epoxy-3-phenyl-1-propanol

Downstream raw materials:

4-(tert-butyl-dimethyl-silanyloxy)-5-[(tert-butyl-dimethyl-silanyloxy)-phenyl-methyl]-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester