(3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate

Base Information

• Chemical Name: (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate
• CAS No.: 137965-33-4
• Molecular Formula: C₇H₈O₃S*C₁₀H₁₀N₂O₄
• Molecular Weight: 394.405
• Mol file: 137965-33-4.mol

Synonyms:(3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate

Chemical Property of (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate

There total 5 articles about (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate 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: 80.0%

toluene-4-sulfonic acid (104-15-4) + (3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone (138125-74-3) → (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate (137965-33-4)

Guidance literature:

With para-thiocresol; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1021/jo00092a025

Reference yield:

p-nitrophenylacetaldehyde (1460-05-5) → (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate (137965-33-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) lithium hexamethyldisilylamide, TiCl(NEt₂)3 / 1.) THF, -78 deg C, 30 min; hexane, -78 deg C, 1 h, 2.) THF, -100 deg C, 10 min; -78 deg C, 3.5 h

2: 85 percent / 6N aq. HCl / Heating

3: 90 percent / 1N aq. NaOH / dioxane / 0.33 h

4: 24 percent / 4-BrC₆H₄SO₂Cl, pyridine / 1.) -45 deg C, 1 h, 2.) 0 deg C, 4 h

5: 80 percent / 4-thiocresol / CH₂Cl₂ / 5 h / 20 °C

With pyridine; hydrogenchloride; sodium hydroxide; titanium tris(diethylamido)chloride; para-thiocresol; 4-bromobenzenesulfonyl chloride; lithium hexamethyldisilazane; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo00092a025

Reference yield:

(2S,3R)-2-<<(2-Nitrophenyl)sulfenyl>amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid (138125-73-2) → (3S,4R)-3-Amino-4-<(4-nitrophenyl)methyl>-2-oxetanone 4-toluenesulfonate (137965-33-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 24 percent / 4-BrC₆H₄SO₂Cl, pyridine / 1.) -45 deg C, 1 h, 2.) 0 deg C, 4 h

2: 80 percent / 4-thiocresol / CH₂Cl₂ / 5 h / 20 °C

With pyridine; para-thiocresol; 4-bromobenzenesulfonyl chloride; In dichloromethane;

DOI:10.1021/jo00092a025

upstream raw materials:

toluene-4-sulfonic acid

(3S,4R)-3-<<(2-Nitrophenyl)sulfenyl>amino>-4-<(4-nitrophenyl)methyl>-2-oxetanone

p-nitrophenylacetaldehyde

(2S,3R)-2-<<(2-Nitrophenyl)sulfenyl>amino>-3-hydroxy-4-(4-nitrophenyl)butanoic acid

Downstream raw materials:

(+)-Obafluorin