threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid

Base Information

• Chemical Name: threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid
• CAS No.: 78560-93-7
• Molecular Formula: C₈H₉NO₄S
• Molecular Weight: 215.23
• Mol file: 78560-93-7.mol

Synonyms:

Chemical Property of threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid

There total 22 articles about threo-trans-6-(α-hydroxyethyl)penem-3-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:

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-15-5,73890-34-3,91685-53-9,91685-54-0) → erythro-trans-6-(1-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1) room temperature, 1 h; 2) reflux, 6 h

2: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

3: 36 percent / acetic acid, water / 1.75 h / Heating

4: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

5: molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

6: thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

7: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

8: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

9: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

10: aq. sodium hydroxide / H₂O / 0.5 h / 0 °C

11: acidic cation exchange resin

With dmap; sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

Reference yield:

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-15-5,73890-34-3,91685-53-9,91685-54-0) → threo-trans-6-(α-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 11 steps

1: 80 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 1) room temperature, 1 h; 2) reflux, 6 h

2: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

3: 19 percent / acetic acid, water / 1.75 h / Heating

4: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

5: 100 percent / molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

6: 100 percent / thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

7: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

8: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

9: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

10: 60 percent / aq. sodium hydroxide / acetonitrile; H₂O / 0.5 h / 0 °C

11: acidic cation exchange resin / H₂O

With dmap; sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

Reference yield:

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.01,7>nonane (73845-16-6,73890-35-4,91685-55-1,91685-56-2) → erythro-trans-6-(1-hydroxyethyl)penem-3-carboxylic acid (73845-25-7,73845-26-8,78560-93-7,78560-94-8,91685-69-7,91685-70-0)

Guidance literature:

Multi-step reaction with 10 steps

1: 100 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1) -10 deg C, 30 min; 2) 0 deg C, 1 h

2: 36 percent / acetic acid, water / 1.75 h / Heating

3: 1.) aq. sodium hydroxide / 1) ethanol, -10 deg C, 5 min; 2) 2 deg C, 80 min

4: molecular sieves / dimethylformamide; toluene / 16 h / 30 °C

5: thionyl chloride, triethylamine / tetrahydrofuran / 0.5 h / 0 °C

6: 2.) aq. sodium carbonate / 1) THF, room temperature, 2 d

7: 1.) ozone, oxygen, trifluoroacetic acid, 2.) dimethyl sulfide, 3.) aq. KHCO₃ / 1) methylene chloride, -20 deg C (15 min); 2) 10 deg C, 10 min; 4) methylene chloride, reflux, 90 min

8: 80 percent / hydrogen / palladium on carbon / aq. ethanol; acetonitrile / 2.5 h / Ambient temperature

9: aq. sodium hydroxide / H₂O / 0.5 h / 0 °C

10: acidic cation exchange resin

With sodium hydroxide; thionyl chloride; molecular sieve; dimethylsulfide; acidic cation exchange resin; water; hydrogen; oxygen; sodium carbonate; potassium hydrogencarbonate; ozone; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja00526a045

upstream raw materials:

Sodium; (5R,6S)-6-((S)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylate

2,2-dimethyl-trans-8-(α-hydroxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane

2,2-dimethyl-trans-8-(α-p-nitrobenzyloxycarbonyloxyethyl)-9-oxo-3-oxa-6-thia-1-azabicyclo<5.2.0^1,7>nonane 6-dioxide