p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate

Base Information

• Chemical Name: p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate
• CAS No.: 123108-06-5
• Molecular Formula: C₂₈H₃₉N₃O₅S₂Si
• Molecular Weight: 589.852
• Mol file: 123108-06-5.mol

Synonyms:

Chemical Property of p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate

There total 14 articles about p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate 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: 54.0%

(3S,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranediylmethyl-4-<(1R)-3-(5-methyl-1,3,4-thidiazol-2-ylthio)-2-oxopropyl>-2-azetidinone (123108-02-1) → p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate (123108-06-5)

Guidance literature:

In toluene; for 1.5h; Heating;

DOI:10.1248/cpb.37.2338

Reference yield:

(3S,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-(1-methyl-2-propynyl)-2-azetidinone (615252-63-6) → p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate (123108-06-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) LDA / 1) THF, hexane, -78 to -40 deg C, 1 h, 2) THF, hexane, -78 deg C to RT then RT, overnight

2: 97 percent / K₂CO₃ / methanol / 5.5 h / Ambient temperature

3: 99 percent / hydrogen, quinoline / 5percent Pd-BaSO₄ / methanol / 0.17 h / Ambient temperature

4: Et₃N / benzene / 10 h / Heating; Dean-Stark trap with mol. sieves 4A

5: m-CPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

6: SOCl₂, 2,6-lutidine / tetrahydrofuran / 3 h / -40 °C

7: 75 percent / 2,6-lutidine / tetrahydrofuran / Ambient temperature

8: 1) n-BuLi / 1) THF, hexane, 30 min, RT, 2) THF, hexane, RT, 15 h

9: 1) DMSO, (CFCO)2O, 3) Et₃N / 1) CH₂Cl₂, -72 deg C, 20 min, 2) CH₂Cl₂, -78 deg C, 30 min, 3) CH₂Cl₂, -78 deg C, 1 h

10: 54 percent / toluene / 1.5 h / Heating

With 2,6-dimethylpyridine; quinoline; n-butyllithium; thionyl chloride; (CFCO)2O; hydrogen; sodium hydrogencarbonate; potassium carbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; palladium on barium sulfate; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.37.2338

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) → p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate (123108-06-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 1) TMSOTf, 2) KF / 1) CH₂Cl₂, 0 deg C, 15 min then 14 h, RT, 2) ether, H₂O, 1 h; var. reag.: BF₃*Et₂O

2: 99 percent / hydrogen, quinoline / 5percent Pd-BaSO₄ / methanol / 0.17 h / Ambient temperature

3: Et₃N / benzene / 10 h / Heating; Dean-Stark trap with mol. sieves 4A

4: m-CPBA, NaHCO₃ / CH₂Cl₂ / 16 h / Ambient temperature

5: SOCl₂, 2,6-lutidine / tetrahydrofuran / 3 h / -40 °C

6: 75 percent / 2,6-lutidine / tetrahydrofuran / Ambient temperature

7: 1) n-BuLi / 1) THF, hexane, 30 min, RT, 2) THF, hexane, RT, 15 h

8: 1) DMSO, (CFCO)2O, 3) Et₃N / 1) CH₂Cl₂, -72 deg C, 20 min, 2) CH₂Cl₂, -78 deg C, 30 min, 3) CH₂Cl₂, -78 deg C, 1 h

9: 54 percent / toluene / 1.5 h / Heating

With 2,6-dimethylpyridine; quinoline; potassium fluoride; n-butyllithium; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; (CFCO)2O; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on barium sulfate; In tetrahydrofuran; methanol; dichloromethane; toluene; benzene;

DOI:10.1248/cpb.37.2338

upstream raw materials:

(3S,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranediylmethyl-4-<(1R)-3-(5-methyl-1,3,4-thidiazol-2-ylthio)-2-oxopropyl>-2-azetidinone

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3R,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-<(1S)-1-methyl-2-propynyl>-2-azetidinone

4(R)-<1-buten-3(S)-yl>-3(S)-<1(R)-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxoazetidine

Downstream raw materials:

p-methoxybenzyl (1S,5R,6S)-6-<(1R)-1-hydroxyethyl>-1-methyl-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate