(5R,6S)-3-{[2-(carbamoyloxy)ethyl]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,6S)-3-{[2-(carbamoyloxy)ethyl]sulfanyl}-6-[(1R)-1-hydroxyethyl]-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
• CAS No.: 95415-91-1
• Molecular Formula: C₁₁H₁₄N₂O₆S₂
• Molecular Weight: 334.374
• Mol file: 95415-91-1.mol

Synonyms:

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

Chemical Property:

• Vapor Pressure: 1.2E-19mmHg at 25°C
• Boiling Point: 650°Cat760mmHg
• Flash Point: 346.9°C
• Density: g/cm³

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

There total 9 articles about (5R,6S)-3-{[2-(carbamoyloxy)ethyl]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:

(3S,4R)-3-<(R)-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (87037-99-8) → (5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylic acid (95415-91-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 95.6 percent / K₂CO₃ / dimethylformamide / 2.5 h / 50 - 55 °C

2: 1) AgNO₃, pyridine, 2) pyridine / 1) MeOH, RT, 2h, 2a) THF, 40 deg C, 0.5h, 2b) 0.75 h, reflux

3: imidazole / tetrahydrofuran / 0.25 h / Ambient temperature

4: 1) lithium hexamethyldisilazide (LiHMDS), 2) glacial HOAc / 1) THF, -40 deg C, 15 min

5: Na₂CO₃ / H₂O / 20 h / Ambient temperature

6: H₃PO₄ / tetrahydrofuran; H₂O / 2.5 h / Ambient temperature

7: 1) PPh₃, 2) sodium 2-ethylhexanoate, (BuO)3P / 1) bis(triisopropylphosphite) palladium dichloride / 1) THF, RT, 15 min, 2) 10 min

With pyridine; 1H-imidazole; tri-n-butyl phosphite; phosphoric acid; sodium carbonate; potassium carbonate; silver nitrate; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; {[(OⁱPr)₃P]₂PdCl₂}; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)90781-1

Reference yield:

(3S,4R)-1-<<(allyloxy)carbonyl>methyl>-3-<(R)-1-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone (90762-39-3) → (5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylic acid (95415-91-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 1) AgNO₃, pyridine, 2) pyridine / 1) MeOH, RT, 2h, 2a) THF, 40 deg C, 0.5h, 2b) 0.75 h, reflux

2: imidazole / tetrahydrofuran / 0.25 h / Ambient temperature

3: 1) lithium hexamethyldisilazide (LiHMDS), 2) glacial HOAc / 1) THF, -40 deg C, 15 min

4: Na₂CO₃ / H₂O / 20 h / Ambient temperature

5: H₃PO₄ / tetrahydrofuran; H₂O / 2.5 h / Ambient temperature

6: 1) PPh₃, 2) sodium 2-ethylhexanoate, (BuO)3P / 1) bis(triisopropylphosphite) palladium dichloride / 1) THF, RT, 15 min, 2) 10 min

With pyridine; 1H-imidazole; tri-n-butyl phosphite; phosphoric acid; sodium carbonate; silver nitrate; acetic acid; triphenylphosphine; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; {[(OⁱPr)₃P]₂PdCl₂}; In tetrahydrofuran; water;

DOI:10.1016/S0040-4020(01)90781-1

Reference yield:

(3S,4R)-1-(allyloxycarbonyl)methyl-3-<(R)-1-hydroxyethyl>-4-sulfhydryl-2-azetidinone (98464-16-5) → (5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylic acid (95415-91-1)

Guidance literature:

Multi-step reaction with 6 steps

1: NEt₃ / CH₂Cl₂ / 0.83 h / 0 °C

2: imidazole / tetrahydrofuran / 0.25 h / Ambient temperature

3: 1) lithium hexamethyldisilazide (LiHMDS), 2) glacial HOAc / 1) THF, -40 deg C, 15 min

4: Na₂CO₃ / H₂O / 20 h / Ambient temperature

5: H₃PO₄ / tetrahydrofuran; H₂O / 2.5 h / Ambient temperature

6: 1) PPh₃, 2) sodium 2-ethylhexanoate, (BuO)3P / 1) bis(triisopropylphosphite) palladium dichloride / 1) THF, RT, 15 min, 2) 10 min

With 1H-imidazole; tri-n-butyl phosphite; phosphoric acid; sodium carbonate; acetic acid; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; sodium 2-ethylhexanoic acid; {[(OⁱPr)₃P]₂PdCl₂}; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/S0040-4020(01)90781-1

upstream raw materials:

allyl (5R,6S)-2-<<2-(carbamoyloxy)ethyl>thio>-6-<(R)-1-hydroxyethyl>penem-3-carboxylate

(3S,4R)-1-(allyloxycarbonyl)methyl-3-<(R)-1-hydroxyethyl>-4-sulfhydryl-2-azetidinone

(2S,5R,6S)-7-Oxo-3-thioxo-6-((R)-1-trimethylsilanyloxy-ethyl)-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid allyl ester

(3S,4R)-3-<(R)-hydroxyethyl>-4-<(triphenylmethyl)thio>-2-azetidinone