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

Base Information

Chemical Name: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
CAS No.:123108-07-6
Molecular Formula:C₂₂H₂₅N₃O₅S₂
Molecular Weight:475.59
Hs Code.:

Synonyms: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

Suppliers and Price of 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

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of 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

There total 21 articles about 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 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: 50.0%

: 123108-06-5
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

: 123108-07-6
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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 29h; Ambient temperature;
DOI:10.1248/cpb.37.2338

Reference yield:

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

: 123108-07-6
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

Guidance literature:: Multi-step reaction with 10 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

10: 50 percent / TBAF / tetrahydrofuran / 29 h / Ambient temperature

With 2,6-dimethylpyridine; quinoline; potassium fluoride; n-butyllithium; thionyl chloride; trimethylsilyl trifluoromethanesulfonate; (CFCO)2O; tetrabutyl ammonium fluoride; 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

Reference yield:

: 615252-63-6
(3S,4R)-3-<(1R)-1-(tert-butyldimethylsilyloxy)ethyl>-4-(1-methyl-2-propynyl)-2-azetidinone

: 123108-07-6
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

Guidance literature:: Multi-step reaction with 11 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

11: 50 percent / TBAF / tetrahydrofuran / 29 h / Ambient temperature

With 2,6-dimethylpyridine; quinoline; n-butyllithium; thionyl chloride; (CFCO)2O; tetrabutyl ammonium fluoride; 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