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

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Chemical Name:(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one
CAS No.:105560-92-7
Molecular Formula:C₂₄H₃₅N₃O₇SSi
Molecular Weight:537.709
Hs Code.:

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

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Chemical Property of (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one

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Technology Process of (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one

There total 7 articles about (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one 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: 90.0%

: 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

: 105459-00-5
<(R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbothioic S-acid

: 105560-92-7
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one

Guidance literature:: With sodium hydroxide; at 0 ℃; 1.) 20 min; 2.) dioxane, 1 h;
DOI:10.1248/cpb.34.999

Reference yield:

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

: 105560-92-7
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 105560-92-7
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<(2R)-N-p-nitrobenzyloxycarbonylpyrrolidin-2-yl>carbonylthioazetidin-2-one

Guidance literature:: Multi-step reaction with 4 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

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