2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate

Base Information

• Chemical Name: 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate
• CAS No.: 76227-79-7
• Molecular Formula: C₁₇H₂₀N₂O₃S
• Molecular Weight: 332.423
• Mol file: 76227-79-7.mol

Synonyms:2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate

Chemical Property of 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate

There total 6 articles about 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate 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: 75.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one (34103-69-0) → 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate (76227-79-7)

Guidance literature:

With N-benzyl-trimethylammonium hydroxide; In N,N-dimethyl-formamide; at -30 - -20 ℃;

DOI:10.1016/S0040-4039(00)77414-4

Reference yield:

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-methyl acetate (76227-77-5) → 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate (76227-79-7)

Guidance literature:

With lithium hexamethyldisilazane; at -60 - 0 ℃; for 2h;

DOI:10.1016/S0040-4039(00)77414-4

Reference yield:

Penicillin G sodium (69-57-8) → 2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-t-butyl acetate (76227-79-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) NaIO₄ / 1) H₂O; 2) NEt₃, DMF, 20 deg C

2: 65 percent Chromat_. / MgSO₄, (CH₃O)3P / benzene / 40 h / Heating

3: 74 percent / KMnO₄, MgSO₄ / H₂O; ethanol / 15 - 20 °C

4: 1) Triton B / 1) DMF, CH₃OH, -30 deg C, 15 min; 0 deg C, 15 min; 2) DMF, 15 min, -30 deg C; 1 h, 0 deg C; 2 h, r. t.

With potassium permanganate; sodium periodate; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; phosphorous acid trimethyl ester; In ethanol; water; benzene;

DOI:10.1016/S0040-4020(01)92143-X

upstream raw materials:

bromoacetic acid tert-butyl ester

(1E,5R)-3-Phenylmethyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-one

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-methyl acetate

Penicillin G sodium

Downstream raw materials:

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-t-butyl malonate

2-<3-phenylacetamido-4-thiochlorocarbonyl-(3R,4R)-azetidin-2-on-1-yl>-t-butyl acetate

2-<3-phenylacetamido-4-ethylthiocarbonate-(3R,4R)-azetidin-2-on-1-yl>-t-butyl acetate

2-<3-benzyl-6-oxo-2-thia-4,7-diaza-(1R,5R)-bicyclo-<3.2.0>-hept-3-en-7-yl>-mono-β-trichloroethyl malonate