(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

Base Information

Chemical Name:(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester
CAS No.:75029-77-5
Molecular Formula:C₂₆H₂₅Cl₃N₂O₇S
Molecular Weight:615.919
Hs Code.:

Synonyms:(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

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Chemical Property of (R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

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Technology Process of (R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

There total 1 articles about (R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic 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

: 17341-93-4
2,2,2-Trichloroethyl chloroformate

: 75029-77-5
(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

Guidance literature:: With pyridine; In dichloromethane;
DOI:10.1021/ja00539a046

Reference yield: 100.0%

: 75029-77-5
(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

: 75029-78-6
3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-2-enoic acid benzyl ester

Guidance literature:: With triethylamine; In benzene;
DOI:10.1021/ja00539a046

Reference yield:

: 75029-77-5
(R)-3-Methyl-2-[(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-(2,2,2-trichloro-ethoxycarbonylsulfanyl)-azetidin-1-yl]-but-3-enoic acid benzyl ester

: (2R,6R,7R)-8-Oxo-7-(2-phenoxy-acetylamino)-5-thia-1,3-diaza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: 100 percent / Et₃N / benzene

2: 77 percent / O₃ / ethyl acetate / -78 °C

3: NaBH₄, AcOH / tetrahydrofuran / 0 °C

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

5: NaN₃ / dimethylformamide / 0 °C

6: H₂ / Pd/C / formic acid

7: acetic acid / 0 °C

8: 86 percent / POCl₃, 2,6-lutidine / CH₂Cl₂ / 0 °C

9: 48 percent / Zn-dust, AcOH / dimethylformamide / 0 °C

10: 100 percent / Na₂CO₃ / tetrahydrofuran; H₂O

With 2,6-dimethylpyridine; sodium tetrahydroborate; thionyl chloride; sodium azide; hydrogen; sodium carbonate; 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