ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate

Base Information

• Chemical Name: ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate
• CAS No.: 870006-35-2
• Molecular Formula: C₁₈H₂₂N₂O₅S
• Molecular Weight: 378.449
• Mol file: 870006-35-2.mol

Synonyms:ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate

Chemical Property of ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate

There total 6 articles about ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate 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: 90.0%

ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1-(tert-butyldiphenylsiloxy)-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate → ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate (870006-35-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/jo051572a

Reference yield: 20.0%

N-benzyl-C-[4-(ethoxycarbonyl)-2-thiazolyl]nitrone (870006-12-5) + (2S)-but-3-ene-1,2-diol (62214-39-5,86161-40-2) → ethyl 2-{(3R,5R)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate + ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate (870006-35-2) + ethyl 2-{(3S,5R)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate (870006-37-4) + ethyl 2-{(3S,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate

Guidance literature:

In ethanol; dichloromethane; at 120 ℃; for 1h; microwave irradiation;

DOI:10.1021/jo051572a

Reference yield:

ethyl 2-(diethoxymethyl)-1,3-thiazole-4-carboxylate (73956-16-8) → ethyl 2-{(3R,5S)-2-benzyl-5-[(2R)-1,2-dihydroxy-2-ethyl]isoxazolidin-3-yl}thiazole-4-carboxylate (870006-35-2)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrochloric acid / acetone / 1 h / Heating

2: 2.17 g / MgSO₄ / CH₂Cl₂ / 6 h / 20 °C

3: 10 percent / CH₂Cl₂; ethanol / 1 h / 120 °C / microwave irradiation

With hydrogenchloride; magnesium sulfate; In ethanol; dichloromethane; acetone;

DOI:10.1021/jo051572a

upstream raw materials:

N-benzyl-C-[4-(ethoxycarbonyl)-2-thiazolyl]nitrone

(2S)-but-3-ene-1,2-diol

ethyl 2-(diethoxymethyl)-1,3-thiazole-4-carboxylate

ethyl 2-formyl-1,3-thiazole-4-carboxylate

Downstream raw materials:

ethyl 2-((3R,5S)-2-benzyl-5-(hydroxymethyl)isoxazolidin-3-yl)thiazole-4-carboxylate