(S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one

Base Information

• Chemical Name: (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one
• CAS No.: 144076-09-5
• Molecular Formula: C₂₀H₂₃NO₄S
• Molecular Weight: 373.473
• Mol file: 144076-09-5.mol

Synonyms:(S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one

Chemical Property of (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one

There total 12 articles about (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one 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: 60.0%

(3S,4R)-5-Benzyloxy-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid (144076-08-4) → (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one (144076-09-5)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89856-2

Reference yield: 60.0%

(3R,4S)-5-Benzyloxy-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid (144076-08-4) → (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one (144076-09-5,144125-95-1)

Guidance literature:

With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1016/S0040-4020(01)89856-2

Reference yield:

benzyl bromide (100-39-0) → (S)-4-((R)-2-Benzyloxy-1-methyl-ethyl)-1-(toluene-4-sulfonyl)-azetidin-2-one (144076-09-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / NaH, Bu₄NI / tetrahydrofuran

3: 97 percent / pyridine / 0.33 h / 0 °C

4: 65 percent / toluene; hexane / 24 h / Heating

5: 80 percent / Jones reagent / acetone / 2 h / -20 °C

6: 60 percent / 4-pyrrolidinopyridine, dicyclohexylcarbodiimide (DCC) / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; jones reagent; tetra-(n-butyl)ammonium iodide; sodium hydride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; acetone; toluene;

DOI:10.1016/S0040-4020(01)89856-2

upstream raw materials:

(3S,4R)-5-Benzyloxy-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid

benzyl bromide

(2S,3R)-4-t-butyldimethylsilyloxy-2,3-epoxy-pentan-1-ol

(Z)-5-<(1,1-dimethylethyl)dimethylsilyloxy>pent-2-en-1-ol