(5R,6R)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (5R,6R)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS No.: 72888-55-2
• Molecular Formula: C₁₀H₁₄N₂O₄S₂
• Molecular Weight: 290.364

Synonyms:

Chemical Property of (5R,6R)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 6.25E-14mmHg at 25°C
• Boiling Point: 540.4°Cat760mmHg
• Flash Point: 280.6°C
• PSA: 154.46000
• Density: 1.62g/cm³
• LogP: 0.48230

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

There total 37 articles about (5R,6R)-3-[(2-aminoethyl)sulfanyl]-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid 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%

(5R,6S)-6-((R)-1-Hydroxy-ethyl)-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (79634-15-4) → (5R,6S)-3-(2-Amino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (72888-55-2)

Guidance literature:

With phosphate buffer; hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 9h;

DOI:10.1248/cpb.29.3158

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (5R,6S)-3-(2-Amino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (72888-55-2)

Guidance literature:

Multi-step reaction with 7 steps

1: methanol / 0.67 h / -10 °C

2: 78 percent / benzene / 5 h / Heating

3: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

4: 17 percent / hydroquinone / xylene / 15 h / 125 - 130 °C

5: hydroquinone / xylene / 7 h / 130 °C

6: 92 percent / tetrabutylammonium fluoride / acetic acid; tetrahydrofuran / 14 h / Ambient temperature

7: 60 percent / hydrogen, 0.1 M phosphate buffer (pH 7.1) / palladium-charcoal (10percent) / tetrahydrofuran / 9 h

With 2,6-dimethylpyridine; thionyl chloride; phosphate buffer; tetrabutyl ammonium fluoride; hydrogen; hydroquinone; palladium on activated charcoal; In tetrahydrofuran; methanol; acetic acid; xylene; benzene;

DOI:10.1248/cpb.29.3158

Reference yield:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylthiocarbonylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester (76855-71-5) → (5R,6S)-3-(2-Amino-ethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid (72888-55-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.)thionyl chloride, 2,6-lutidine 2.) 2,6-lutidine / 1.) THF, -15 deg C, 15 min, 2.) THF, 75 deg C, 42 h

2: 17 percent / hydroquinone / xylene / 15 h / 125 - 130 °C

3: hydroquinone / xylene / 7 h / 130 °C

4: 92 percent / tetrabutylammonium fluoride / acetic acid; tetrahydrofuran / 14 h / Ambient temperature

5: 60 percent / hydrogen, 0.1 M phosphate buffer (pH 7.1) / palladium-charcoal (10percent) / tetrahydrofuran / 9 h

With 2,6-dimethylpyridine; thionyl chloride; phosphate buffer; tetrabutyl ammonium fluoride; hydrogen; hydroquinone; palladium on activated charcoal; In tetrahydrofuran; acetic acid; xylene;

DOI:10.1248/cpb.29.3158

upstream raw materials:

(5R,6R)-3-(2-Allyloxycarbonylamino-ethylsulfanyl)-6-((S)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

1-(t-butyldimethylsilyl)-3-(1-hydroxyethyl)-4-ethylthioazetidin-2-one

Carbonic acid 1-(2-ethylsulfanyl-4-oxo-azetidin-3-yl)-ethyl ester 2,2,2-trichloro-ethyl ester

Carbonic acid 1-[1-(tert-butyl-dimethyl-silanyl)-2-ethylsulfanyl-4-oxo-azetidin-3-yl]-ethyl ester 2,2,2-trichloro-ethyl ester

Refernces

2-(Alkylthio)penem-3-carboxylic acids. V. Synthesis and antibacterial activities of '1-thiathienamycin' and related compounds

10.1248/cpb.29.3158

The research focuses on the synthesis and antibacterial activities of "1-thiathienamycin" and related compounds, which are part of the 2-(alkylthio)penem-3-carboxylic acid family. The purpose of this study was to determine if the hydroxyethyl group at the C-6 position, the natural side chain of thienamycin, would enhance the antibacterial potency of the parent penems. The researchers synthesized optically active "1-thiathienamycin" and other (hydroxyethyl)penemcarboxylic acids from 8R and 8S azetidinones via an intramolecular Wittig reaction of the trithiocarbonatephosphoranes. The study concluded that the introduction of the C-6 hydroxyethyl group generally increased activity against β-lactamase-producing strains, and the 8R trans diastereomers showed far more potent activity than the corresponding 8S trans diastereomers. Notably, the 8R penems with the amino function in the side chain exhibited outstanding anti-Pseudomonas activity. Chemicals used in the process included 2-(alkylthio)penem-3-carboxylic acids, azetidinones, trithiocarbonates, phosphoranes, and various reagents for the intramolecular Wittig reaction and subsequent transformations.

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