p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

Base Information

Chemical Name:p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate
CAS No.:105420-48-2
Molecular Formula:C₃₄H₄₄N₄O₁₂SSi
Molecular Weight:760.894
Hs Code.:

p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

Synonyms:p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

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Chemical Property of p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

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Technology Process of p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

There total 10 articles about p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate 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: 76.0%

: 64370-35-0
p-nitrobenzyl glyoxylate

: 105420-41-5,105498-53-1
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS)-N-p-nitrobenzyloxycarbonylpiperidin-2-yl>carbonylthioazetidin-2-one

: 105420-48-2
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

Guidance literature:: With triethylamine; In benzene; for 2h; Heating;
DOI:10.1248/cpb.34.999

Reference yield:

: 80629-46-5
methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate

: 105420-48-2
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 1.) silver acetate, activated zinc powder; 2.) allyl bromide / 1.) acetic acid, 110-120 deg C, 1 min; 2.) methanol, -20 deg C, 20 min

2: 51 percent / imidazole / dimethylformamide

3: 90 percent / mercuric acetate / 1.5 h / 90 °C

4: 83 percent / KMnO₄ in water / acetic acid; acetone / 3 h / Ambient temperature

5: 63 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 h

6: 76 percent / triethylamine / benzene / 2 h / Heating

With 1H-imidazole; sodium hydroxide; potassium permanganate; mercury(II) diacetate; silver(I) acetate; triethylamine; allyl bromide; zinc; In acetic acid; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.34.999

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105420-48-2
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(RS-N-p-nitrobenzyloxycarbonylpiperidin-2-yl)carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

Guidance literature:: Multi-step reaction with 5 steps

1: 51 percent / imidazole / dimethylformamide

2: 90 percent / mercuric acetate / 1.5 h / 90 °C

3: 83 percent / KMnO₄ in water / acetic acid; acetone / 3 h / Ambient temperature

4: 63 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 h

5: 76 percent / triethylamine / benzene / 2 h / Heating

With 1H-imidazole; sodium hydroxide; potassium permanganate; mercury(II) diacetate; triethylamine; In acetic acid; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.34.999