(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Base Information

Chemical Name:(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone
CAS No.:92838-73-8
Molecular Formula:C₂₅H₂₆N₄O₁₁
Molecular Weight:558.502
Hs Code.:

Synonyms:(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

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Chemical Property of (3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

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Technology Process of (3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

There total 8 articles about (3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-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: 70.0%

: 96542-75-5
(3S,4R)-3-<(R)-1-hydroxyethyl>-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-2-azetidinone

: 4457-32-3
4-nitrobenzyl chloroformate

: 92838-73-8
(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: With dmap; In dichloromethane;
DOI:10.1016/S0040-4039(00)98475-2

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

: 92838-73-8
(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / boron trifluoride etherate / CH₂Cl₂ / 15 h / Ambient temperature

2: 650 mg / m-chloroperbenzoic acid / CH₂Cl₂ / 15 h / Ambient temperature

3: 77 percent / dimethylformamide / 15 h / Ambient temperature

4: 1.) H₂; 2.) N,N-diisopropylethylamine / 1.) PtO₂ / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH₂Cl₂, roomtemp.

5: 66 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

6: 90 percent / boron trifluoride etherate / acetonitrile / 0.3 h

7: 66 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

With dmap; boron trifluoride diethyl etherate; hydrogen; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; platinum(IV) oxide; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1246/bcsj.59.1363

Reference yield:

: 92838-69-2,96613-74-0,96613-75-1
(3S,4R)-4-(3-cyano-2-hydroxypropyl)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-2-azetidinone

: 92838-73-8
(3S,4R)-4-<4-(p-nitrobenzyloxycarbonylamino)-2-oxobutyl>-3-<(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) H₂; 2.) N,N-diisopropylethylamine / 1.) PtO₂ / 1.) glacial AcOH, 1 atm, 5 h; 2.) CH₂Cl₂, roomtemp.

2: 66 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

3: 90 percent / boron trifluoride etherate / acetonitrile / 0.3 h

4: 66 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 0.5 h

With dmap; boron trifluoride diethyl etherate; hydrogen; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; platinum(IV) oxide; In dichloromethane; acetonitrile;
DOI:10.1246/bcsj.59.1363