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

Base Information

Chemical Name:p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate
CAS No.:105499-15-8
Molecular Formula:C₅₁H₅₅N₄O₁₁PSSi
Molecular Weight:991.143
Hs Code.:

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

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

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

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

There total 13 articles about p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate 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:

: 87596-66-5
2-{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-1-[chloro-(4-nitro-benzyloxycarbonyl)-methyl]-4-oxo-azetidin-2-ylsulfanylcarbonyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

: 105499-15-8
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: With 2,6-dimethylpyridine; In tetrahydrofuran; at 50 - 60 ℃; for 0.333333h; Yield given;
DOI:10.1248/cpb.34.999

Reference yield:

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

: 105499-15-8
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: Multi-step reaction with 8 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: 90 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1 h

6: 82 percent / triethylamine / benzene / 2 h / Heating

7: 2,6-lutidine, SOCl₂ / tetrahydrofuran / 1 h / -20 °C

8: 2,6-lutidine / tetrahydrofuran / 0.33 h / 50 - 60 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; potassium permanganate; thionyl chloride; mercury(II) diacetate; silver(I) acetate; triethylamine; allyl bromide; zinc; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.34.999

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105499-15-8
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-triphenylphosphoranylideneacetate

Guidance literature:: Multi-step reaction with 7 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: 90 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1 h

5: 82 percent / triethylamine / benzene / 2 h / Heating

6: 2,6-lutidine, SOCl₂ / tetrahydrofuran / 1 h / -20 °C

7: 2,6-lutidine / tetrahydrofuran / 0.33 h / 50 - 60 °C

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; potassium permanganate; thionyl chloride; mercury(II) diacetate; triethylamine; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1248/cpb.34.999