(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Base Information

Chemical Name:(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one
CAS No.:75321-06-1
Molecular Formula:C₂₂H₃₂N₂O₇Si
Molecular Weight:464.591
Hs Code.:

Synonyms:(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

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Chemical Property of (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

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Technology Process of (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

There total 9 articles about (3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one 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: 86.0%

: 105995-50-4
magnesium 4-nitrobenzyl malonate

: 75333-88-9
(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-1-hydroxy-ethyl)-4-(2-imidazol-1-yl-2-oxo-ethyl)-azetidin-2-one

: 75321-06-1
(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Guidance literature:: In tetrahydrofuran; Ambient temperature;
DOI:10.1021/ja00539a040

Reference yield:

: 74288-30-5
(4S)-1-(t-butyldimethylsilyl)-4-iodomethyl-azetidin-2-one

: 75321-06-1
(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 80 percent / tetrahydrofuran / -78 °C

2: 82 percent Turnov_. / LDA / tetrahydrofuran / -78 °C

3: K-Selectride, KI / diethyl ether / 25 °C

4: 93 percent / HgCl₂, HgO / methanol; H₂O / Heating

5: 76 percent / hydrogen peroxide / methanol; H₂O

6: tetrahydrofuran / Ambient temperature

7: 86 percent / tetrahydrofuran / Ambient temperature

With dihydrogen peroxide; potassium tri-sec-butyl-borohydride; potassium iodide; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water;
DOI:10.1021/ja00539a040

Reference yield:

: 75321-01-6
(S)-1-(tert-Butyl-dimethyl-silanyl)-4-(2-trimethylsilanyl-[1,3]dithian-2-ylmethyl)-azetidin-2-one

: 75321-06-1
(3S,4R)-1-(t-butyldimethylsilyl)-3-[(R)-1-hydroxyethyl]-4-(3-p-nitrobenzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent Turnov_. / LDA / tetrahydrofuran / -78 °C

2: K-Selectride, KI / diethyl ether / 25 °C

3: 93 percent / HgCl₂, HgO / methanol; H₂O / Heating

4: 76 percent / hydrogen peroxide / methanol; H₂O

5: tetrahydrofuran / Ambient temperature

6: 86 percent / tetrahydrofuran / Ambient temperature

With dihydrogen peroxide; potassium tri-sec-butyl-borohydride; potassium iodide; mercury dichloride; mercury(II) oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; water;
DOI:10.1021/ja00539a040