p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

Base Information

Chemical Name:p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate
CAS No.:126579-15-5
Molecular Formula:C₂₂H₃₂N₂O₇Si
Molecular Weight:464.591
Hs Code.:

Synonyms:p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

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Chemical Property of p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

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Technology Process of p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

There total 5 articles about p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate 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: 87.0%

p-nitrobenzyl (2R,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)-oxy>ethyl>-2-(2,3-dihydroxypropyl)-4-oxo-1-azetidineacetate: 126579-13-3
p-nitrobenzyl (2R,3S)-3-<(R)-1-<(tert-butyldimethylsilyl)-oxy>ethyl>-2-(2,3-dihydroxypropyl)-4-oxo-1-azetidineacetate

: 126579-15-5
p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

Guidance literature:: With periodic acid; In tetrahydrofuran; at 0 ℃; for 0.5h;
DOI:10.1021/jo00297a026

Reference yield:

: 16869-24-2
4-nitrobenzyl bromoacetate

: 126579-15-5
p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

Guidance literature:: Multi-step reaction with 3 steps

1: 1) potassium tert-butoxide / 1) toluene, 0 deg C, 30 min; 2) toluene, -30 deg C, 20 min

2: 100 percent / osmium tetroxide / dioxane / 20 h / Ambient temperature

3: 87 percent / periodic acid / tetrahydrofuran / 0.5 h / 0 °C

With osmium(VIII) oxide; potassium tert-butylate; periodic acid; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jo00297a026

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

: 126579-15-5
p-nitrobenzyl (3S,4R)-3<(R)-1-<(tert-butyldimethylsilyl)oxy>ethyl>-2-oxo-4-(2-oxoethyl)-1-azetidineacetate

Guidance literature:: Multi-step reaction with 4 steps

1: 1) cuprous iodide / 1) THF, -15 deg C, 15 min; 2) THF, 10 min at -30 deg C, then 1 h at 10 deg C

2: 1) potassium tert-butoxide / 1) toluene, 0 deg C, 30 min; 2) toluene, -30 deg C, 20 min

3: 100 percent / osmium tetroxide / dioxane / 20 h / Ambient temperature

4: 87 percent / periodic acid / tetrahydrofuran / 0.5 h / 0 °C

With copper(l) iodide; osmium(VIII) oxide; potassium tert-butylate; periodic acid; In tetrahydrofuran; 1,4-dioxane;
DOI:10.1021/jo00297a026