1-Pyrrolidinecarboxylic acid, 2-[2-[[3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-[1-hydroxy-2-[(4- nitrophenyl)methoxy]-2-oxoethyl]-4-oxo-2-azetidinyl]thio]-2-oxoethyl]-, (4-nitrophenyl)methyl ester

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2-[2-[[3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-[1-hydroxy-2-[(4- nitrophenyl)methoxy]-2-oxoethyl]-4-oxo-2-azetidinyl]thio]-2-oxoethyl]-, (4-nitrophenyl)methyl ester
• CAS No.: 105439-66-5
• Molecular Formula: C₃₄H₄₄N₄O₁₂SSi
• Molecular Weight: 760.894
• Mol file: 105439-66-5.mol

Synonyms:

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2-[2-[[3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-[1-hydroxy-2-[(4- nitrophenyl)methoxy]-2-oxoethyl]-4-oxo-2-azetidinyl]thio]-2-oxoethyl]-, (4-nitrophenyl)methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-Pyrrolidinecarboxylic acid, 2-[2-[[3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-[1-hydroxy-2-[(4- nitrophenyl)methoxy]-2-oxoethyl]-4-oxo-2-azetidinyl]thio]-2-oxoethyl]-, (4-nitrophenyl)methyl ester

There total 24 articles about 1-Pyrrolidinecarboxylic acid, 2-[2-[[3-[1-[[(1,1-dimethylethyl)dimethylsilyl]oxy]ethyl]-1-[1-hydroxy-2-[(4- nitrophenyl)methoxy]-2-oxoethyl]-4-oxo-2-azetidinyl]thio]-2-oxoethyl]-, (4-nitrophenyl)methyl ester 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: 72.0%

p-nitrobenzyl glyoxylate (64370-35-0) + (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>acetylthio>azetidin-2-one (105420-43-7) → p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<((2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl)acetylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate (105439-66-5)

Guidance literature:

With triethylamine; In benzene; for 2h; Heating;

DOI:10.1248/cpb.34.999

Reference yield: 51.0%

p-nitrobenzyl glyoxylate (64370-35-0) + (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>acetylthio>azetidin-2-one (105499-98-7) → p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<((2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl)acetylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate (105439-66-5)

Guidance literature:

With triethylamine; In benzene; for 2h; Heating;

DOI:10.1248/cpb.34.999

Reference yield:

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate (80629-46-5) → p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<((2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl)acetylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate (105439-66-5)

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: 1.0 g / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 h

6: 51 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

upstream raw materials:

p-nitrobenzyl glyoxylate

(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>acetylthio>azetidin-2-one

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

methyl (3S,5R,6S)-6-<(1R)-(tert-butyldimethylsiloxy)ethyl>penicillanate

Downstream raw materials:

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

p-nitrobenzyl (5R,6S)-6-<(1R)-(tert-butyldimethylsiloxy)ethyl>-2-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>methyl-2-penem-3-carboxylate

p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>methyl-2-penem-3-carboxylate

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