(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

Base Information

Chemical Name:(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone
CAS No.:88139-49-5
Molecular Formula:C₃₈H₃₁N₂O₆P
Molecular Weight:642.648
Hs Code.:

Synonyms:(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

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

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Chemical Property of (4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

Chemical Property:

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Technology Process of (4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

There total 6 articles about (4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone 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:

: 88139-48-4
(4R)-1-(p-nitrobenzyloxycarbonyl)chloromethyl-4-phenacyl-2-azetidinone

: 603-35-0
triphenylphosphine

: 88139-49-5
(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 2 ℃; for 19h; Yield given;
DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

: 14252-44-9
bis(methylthio)phenylmethane

: 88139-49-5
(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 1) n-BuLi / 1) THF, hexane, -23 deg C -> -20 deg C, 1 h, 2) THF, 1 h, -78 deg C -> 0 deg C, 1 h

2: 98 percent / HgO, HgCl₂ / methanol / 0.5 h / Ambient temperature

3: 81 percent / MeOH, H₂O, 1 N HCl / tetrahydrofuran / 15 h / Ambient temperature

4: 77 percent / toluene / 8 h / Heating

5: 96 percent / thionylchloride, Amberlyst A₂₁ / CH₂Cl₂ / 3 h / -18 deg C -> 0 deg C

6: 2) 5percent NaHCO₃ aq / dimethylformamide / 19 h / 2 °C

With hydrogenchloride; methanol; n-butyllithium; thionyl chloride; amberlyst A₂₁; water; sodium hydrogencarbonate; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

: 88139-46-2
(4R)-4-phenacyl-azetidin-2-one

: 88139-49-5
(4R)-1-(p-nitrobenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-phenacyl-2-azetidinone

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / toluene / 8 h / Heating

2: 96 percent / thionylchloride, Amberlyst A₂₁ / CH₂Cl₂ / 3 h / -18 deg C -> 0 deg C

3: 2) 5percent NaHCO₃ aq / dimethylformamide / 19 h / 2 °C

With thionyl chloride; amberlyst A₂₁; sodium hydrogencarbonate; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/S0040-4020(01)92147-7