benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Base Information

Chemical Name:benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate
CAS No.:74643-20-2
Molecular Formula:C₄₀H₃₅N₂O₇PS
Molecular Weight:718.767
Hs Code.:

Synonyms:benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

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Chemical Property of benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

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Technology Process of benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

There total 7 articles about benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate 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

: 74643-20-2
benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: Multi-step reaction with 7 steps

1: 7.00 g / pyridine / CH₂Cl₂ / 0.25 h / -15 °C

2: 30 percent / Et₃N / benzene / 1.17 h / Ambient temperature

3: 87 percent / O₃ / ethyl acetate / -78 °C

4: 1.88 g / 1.) Al-Hg; 2.) AcOH, H₂O / 5 °C / 1.) THF; 2.) 70 min

5: 1.) 2,6-lutidine; 2.) SOCl₂ / CH₂Cl₂ / 1.) -40 deg C; 2.) -40 -> -5 deg C, 30 min

6: 1.11 g / CH₂Cl₂ / 5.5 h / Heating

7: 0.56 g / Zn dust, AcOH / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; thionyl chloride; aluminium amalgam; water; ozone; acetic acid; triethylamine; zinc; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)97686-0

Reference yield:

: 78549-42-5
benzyl (2R)-2-<(3R,4R)-3-phenoxyacetamido-4-trichloroethoxycarbonyloxyacetylthio-2-oxoazetidin-1-yl>-3-methylbut-3-enoate

: 74643-20-2
benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: Multi-step reaction with 6 steps

1: 30 percent / Et₃N / benzene / 1.17 h / Ambient temperature

2: 87 percent / O₃ / ethyl acetate / -78 °C

3: 1.88 g / 1.) Al-Hg; 2.) AcOH, H₂O / 5 °C / 1.) THF; 2.) 70 min

4: 1.) 2,6-lutidine; 2.) SOCl₂ / CH₂Cl₂ / 1.) -40 deg C; 2.) -40 -> -5 deg C, 30 min

5: 1.11 g / CH₂Cl₂ / 5.5 h / Heating

6: 0.56 g / Zn dust, AcOH / CH₂Cl₂ / 1 h / Ambient temperature

With 2,6-dimethylpyridine; thionyl chloride; aluminium amalgam; water; ozone; acetic acid; triethylamine; zinc; In dichloromethane; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)97686-0

Reference yield:

: 73885-12-8,74643-18-8,74643-19-9
Chloro-{(3R,4R)-2-oxo-3-(2-phenoxy-acetylamino)-4-[2-(2,2,2-trichloro-ethoxycarbonyloxy)-acetylsulfanyl]-azetidin-1-yl}-acetic acid benzyl ester

: 74643-20-2
benzyl 2-<(3R,4R)-3-phenoxyacetamido-4-hydroxyacetylthio-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: Multi-step reaction with 2 steps

1: 1.11 g / CH₂Cl₂ / 5.5 h / Heating

2: 0.56 g / Zn dust, AcOH / CH₂Cl₂ / 1 h / Ambient temperature

With acetic acid; zinc; In dichloromethane;
DOI:10.1016/S0040-4020(01)97686-0