1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine

Base Information

• Chemical Name: 1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine
• CAS No.: 865758-86-7
• Molecular Formula: C₁₇H₂₁NO₄
• Molecular Weight: 303.358
• Mol file: 865758-86-7.mol

Synonyms:1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine

Chemical Property of 1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine

There total 1 articles about 1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine 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: 50.0%

1-[(2S,3S)-2-((S)-1-Benzyloxy-allyl)-3-hydroxy-3,6-dihydro-2H-pyridin-1-yl]-ethanone (791821-67-5) → 1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine (865758-86-7)

Guidance literature:

With tert.-butylhydroperoxide; vanadyl acetylacetonate; In decane; dichloromethane; at 25 ℃; for 5h;

DOI:10.1016/j.tet.2005.07.014

Reference yield: 55.0%

1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine (865758-86-7) → 1-acetyl-2-(1-benzyloxyallyl)-3,4,5-trihydroxypiperidine (865758-87-8)

Guidance literature:

With sodium benzoate; at 130 ℃; for 12h;

DOI:10.1016/j.tet.2005.07.014

Reference yield:

1-acetyl-2-(1-benzyloxyallyl)-3-hydroxy-4,5-epoxypiperidine (865758-86-7) → Benzoic acid (1R,2R,6S,7R,8R,8aR)-1,6,7,8-tetrakis-benzyloxy-octahydro-indolizin-2-yl ester (865758-93-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 55 percent / aq. sodium benzoate / 12 h / 130 °C

2.1: NaH / dimethylformamide / 0.5 h / 0 °C

2.2: 94 percent / dimethylformamide / 2 h

3.1: 78 percent / NMO; OsO₄ / acetone; H₂O / 4 h / 25 °C

4.1: aq. HCl / 4 h / 70 °C

4.2: 74 percent / PPh₃; molecular sieves; DEAD / pyridine / 4 h / 0 °C

5.1: 62 mg / PPh₃; DEAD / tetrahydrofuran / 12 h / 25 °C

With hydrogenchloride; sodium benzoate; osmium(VIII) oxide; N-methyl-2-indolinone; sodium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone; 4.2: Mitsunobu cyclization / 5.1: Mitsunobu reaction;

DOI:10.1016/j.tet.2005.07.014

upstream raw materials:

1-[(2S,3S)-2-((S)-1-Benzyloxy-allyl)-3-hydroxy-3,6-dihydro-2H-pyridin-1-yl]-ethanone

Downstream raw materials:

1-acetyl-2-(1-benzyloxyallyl)-3,4,5-trihydroxypiperidine

2-(1-benzyloxy-3-hydroxypropyl)-3,4,5-tribenzyloxypiperidine

1,6,7,8-tetrabenzyloxy-2-hydroxyindolizidine

1,6,7,8-tetrabenzyloxy-2-hydroxyindolizidine