ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate

Base Information

• Chemical Name: ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate
• CAS No.: 501648-84-6
• Molecular Formula: C₁₉H₂₀N₂O₁₁S
• Molecular Weight: 484.441
• Mol file: 501648-84-6.mol

Synonyms:ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate

Chemical Property of ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate

There total 7 articles about ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate 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: 75.0%

ethyl (2R,3S)-2,3-dihydroxy-5-(4-nitrophenoxy)pentanoate (501648-83-5) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate (501648-84-6)

Guidance literature:

In pyridine; at 0 ℃; for 24h;

DOI:10.1002/1522-2675(200210)85:10<3090::AID-HLCA3090>3.0.CO;2-8

Reference yield:

ethyl (4R,5S)-5-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate (501648-79-9) → ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate (501648-84-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / H₂ / 10 percent Pd/C / ethanol / 18 h / 20 °C

2: 90 percent / PPh₃; 1H-imidazole; I₂ / CH₂Cl₂ / 2 h / 20 °C

3: 89 percent / dimethylformamide / 16 h / 50 °C

4: 70 percent / TsOH / ethanol / 20 h / 50 °C

5: 75 percent / pyridine / 24 h / 0 °C

With 1H-imidazole; hydrogen; iodine; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; In pyridine; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/1522-2675(200210)85:10<3090::AID-HLCA3090>3.0.CO;2-8

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate (501648-84-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / NaHCO3; MeSO2NH2; AD-mix-α / H2O; 2-methyl-propan-2-ol / 24 h / 0 °C

2: 98 percent / TsOH / acetone / 1.5 h / 20 °C

3: 99 percent / H₂ / 10 percent Pd/C / ethanol / 18 h / 20 °C

4: 90 percent / PPh₃; 1H-imidazole; I₂ / CH₂Cl₂ / 2 h / 20 °C

5: 89 percent / dimethylformamide / 16 h / 50 °C

6: 70 percent / TsOH / ethanol / 20 h / 50 °C

7: 75 percent / pyridine / 24 h / 0 °C

With 1H-imidazole; AD-mix-α; methanesulfonamide; hydrogen; iodine; sodium hydrogencarbonate; toluene-4-sulfonic acid; triphenylphosphine; palladium on activated charcoal; toluene-4-sulfonic acid; In pyridine; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1002/1522-2675(200210)85:10<3090::AID-HLCA3090>3.0.CO;2-8

upstream raw materials:

ethyl (2R,3S)-2,3-dihydroxy-5-(4-nitrophenoxy)pentanoate

2-Nitrobenzenesulfonyl chloride

ethyl (4R,5S)-5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxolidine-4-carboxylate

ethyl (4R,5S)-5-(2-iodoethyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate