Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester
• CAS No.: 210217-89-3
• Molecular Formula: C₁₉H₂₁NO₁₁
• Molecular Weight: 439.376
• Mol file: 210217-89-3.mol

Synonyms:Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester

Chemical Property of Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester

There total 5 articles about Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester 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: 23.0%

4-nitrophenyl 2,3,4-tri-O-acetyl-6,7-dideoxy-β-D-galacto-hept-6-enopyranoside (210217-82-6) → Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester (210217-89-3) + Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(R)-oxiranyl-tetrahydro-pyran-3-yl ester (210217-83-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 80h; Ambient temperature;

DOI:10.1016/S0008-6215(97)00246-2

Reference yield:

4-nitro-phenol (100-02-7,78813-13-5,89830-32-0) → Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester (210217-89-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 65 percent / benzyltriethylammonium chloride, NaOH / CHCl₃; H₂O / 3 h / Heating

2: 100 percent / H₂ / Lindlar's catalyst / ethyl acetate / 3 h / Ambient temperature

3: 66 percent / m-CPBA / CH₂Cl₂ / 80 h / Ambient temperature

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In dichloromethane; chloroform; water; ethyl acetate;

DOI:10.1016/S0008-6215(97)00246-2

Reference yield:

Acetic acid (3R,4S,5S,6R)-2,3,5-triacetoxy-6-ethynyl-tetrahydro-pyran-4-yl ester → Acetic acid (2R,3S,4S,5R,6S)-4,5-diacetoxy-6-(4-nitro-phenoxy)-2-(S)-oxiranyl-tetrahydro-pyran-3-yl ester (210217-89-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 79 percent / 30percent HBr / acetic acid / 2.5 h / 0 °C

2: 65 percent / benzyltriethylammonium chloride, NaOH / CHCl₃; H₂O / 3 h / Heating

3: 100 percent / H₂ / Lindlar's catalyst / ethyl acetate / 3 h / Ambient temperature

4: 66 percent / m-CPBA / CH₂Cl₂ / 80 h / Ambient temperature

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; hydrogen bromide; hydrogen; 3-chloro-benzenecarboperoxoic acid; Lindlar's catalyst; In dichloromethane; chloroform; water; acetic acid; ethyl acetate;

DOI:10.1016/S0008-6215(97)00246-2

upstream raw materials:

4-nitrophenyl 2,3,4-tri-O-acetyl-6,7-dideoxy-β-D-galacto-hept-6-enopyranoside

4-nitro-phenol

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-bromo-6-ethynyl-tetrahydro-pyran-4-yl ester

Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-ethynyl-2-(4-nitro-phenoxy)-tetrahydro-pyran-3-yl ester