(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester
CAS No.:78854-81-6
Molecular Formula:C₂₃H₂₃N₃O₆S
Molecular Weight:469.518
Hs Code.:

Synonyms:(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

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Chemical Property of (2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

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Technology Process of (2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

There total 11 articles about (2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester 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:

: 68047-65-4
(R)-2-[(2R)-2r-mercapto-4-oxo-3c-(2-phenoxy-acetylamino)-azetidin-1-yl]-3-methyl-but-3-enoic acid benzyl ester

: 78854-81-6
(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: pyridine / CH₂Cl₂

2: 100 percent / Et₃N / benzene

3: 77 percent / O₃ / ethyl acetate / -78 °C

4: NaBH₄, AcOH / tetrahydrofuran / 0 °C

5: SOCl₂, 2,6-lutidine / CH₂Cl₂ / -35 - 0 °C

6: NaN₃ / dimethylformamide / 0 °C

7: H₂ / Pd/C / formic acid

8: acetic acid / 0 °C

9: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

10: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

11: 88 percent / Al/Hg / tetrahydrofuran; H₂O / 5 - 10 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; aluminum amalgam; thionyl chloride; sodium azide; hydrogen; ozone; acetic acid; triethylamine; zinc; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; formic acid; dichloromethane; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ja00539a046

Reference yield:

: 75029-79-7
Oxo-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-acetic acid benzyl ester

: 78854-81-6
(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: NaBH₄, AcOH / tetrahydrofuran / 0 °C

2: SOCl₂, 2,6-lutidine / CH₂Cl₂ / -35 - 0 °C

3: NaN₃ / dimethylformamide / 0 °C

4: H₂ / Pd/C / formic acid

5: acetic acid / 0 °C

6: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

7: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

8: 88 percent / Al/Hg / tetrahydrofuran; H₂O / 5 - 10 °C

With 2,6-dimethylpyridine; sodium tetrahydroborate; aluminum amalgam; thionyl chloride; sodium azide; hydrogen; acetic acid; zinc; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; formic acid; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00539a046

Reference yield:

: 75029-80-0,75045-65-7,76985-72-3
Hydroxy-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-acetic acid benzyl ester

: 78854-81-6
(2S,6R,7R)-3-Acetyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]octane-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: SOCl₂, 2,6-lutidine / CH₂Cl₂ / -35 - 0 °C

2: NaN₃ / dimethylformamide / 0 °C

3: H₂ / Pd/C / formic acid

4: acetic acid / 0 °C

5: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

6: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

7: 88 percent / Al/Hg / tetrahydrofuran; H₂O / 5 - 10 °C

With 2,6-dimethylpyridine; aluminum amalgam; thionyl chloride; sodium azide; hydrogen; acetic acid; zinc; trichlorophosphate; palladium on activated charcoal; In tetrahydrofuran; formic acid; dichloromethane; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/ja00539a046