(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

Base Information

Chemical Name:(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone
CAS No.:90629-15-5
Molecular Formula:C₃₉H₄₆N₃O₁₄PS
Molecular Weight:843.846
Hs Code.:

(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

Synonyms:(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

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Chemical Property of (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

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Technology Process of (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

There total 7 articles about (3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-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: 85.0%

: 90629-15-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

Guidance literature:

Reference yield:

: 76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1
(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

: 90629-15-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

Guidance literature:: Multi-step reaction with 6 steps

1: 100 percent / Et₃N / tetrahydrofuran / 2 h / Ambient temperature

2: 1) trimethylsilyl trifluoromethanesulfonate

3: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

4: 45 percent / DMAP / CH₂Cl₂

5: Et₃N / CH₂Cl₂ / 0 °C

6: toluene / 80 - 90 °C / 1-3 hrs

With dmap; boron trifluoride diethyl etherate; triethylamine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

: 86978-81-6
(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

: 90629-15-5
(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-1-[1-(p-nitrobenzyloxycarbonyl)-1-triisopropoxyphosphoranylidenemethyl]-4-[(phenylthio)carbonylmethyl]-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 1) trimethylsilyl trifluoromethanesulfonate

2: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

3: 45 percent / DMAP / CH₂Cl₂

4: Et₃N / CH₂Cl₂ / 0 °C

5: toluene / 80 - 90 °C / 1-3 hrs

With dmap; boron trifluoride diethyl etherate; triethylamine; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; toluene; acetonitrile;
DOI:10.1016/S0040-4039(01)81292-2