(S)-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

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Chemical Name:(S)-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
CAS No.:87596-66-5
Molecular Formula:C₃₃H₄₁ClN₄O₁₁SSi
Molecular Weight:765.313
Hs Code.:

(S)-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

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Chemical Property of (S)-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

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Technology Process of (S)-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

There total 24 articles about (S)-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 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:

: 87596-65-4
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

: 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

Guidance literature:: With 2,6-dimethylpyridine; thionyl chloride; In tetrahydrofuran; at -20 ℃; for 1h;
DOI:10.1248/cpb.34.999

Reference yield:

: 87596-65-4
p-nitrobenzyl 2-<(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<<(2S)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthio>-2-oxoazetidin-1-yl>-2-hydroxyacetate

: 87596-66-5
(S)-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

Guidance literature:: With 2,6-dimethylpyridine; thionyl chloride; In tetrahydrofuran; at -20 ℃; for 0.5h;
DOI:10.1248/cpb.34.999

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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