(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Base Information

Chemical Name:(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one
CAS No.:105499-99-8
Molecular Formula:C₂₄H₃₇N₃O₇SSi
Molecular Weight:539.725
Hs Code.:

Synonyms:(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Suppliers and Price of (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

There total 14 articles about (3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-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: 99.0%

: 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

: 87154-01-6
5-(p-nitrobenzyloxycarbonylamino)pentanethioic S-acid

: 105499-99-8
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Guidance literature:: With sodium hydroxide; at 0 ℃; 1.) 20 min; 2.) dioxane, 1.5 h;
DOI:10.1248/cpb.34.999

Reference yield: 98.0%

: 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

: 87154-01-6
5-(p-nitrobenzyloxycarbonylamino)pentanethioic S-acid

: 81225-34-5,85646-83-9,85646-84-0,85701-25-3,105499-99-8,105561-22-6
dl-(3R*,4S*)-3-<(1R*)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-2-one

Guidance literature:: With sodium hydroxide; at 0 ℃; 1.) 20 min; 2.) dioxane, 1.5 h;
DOI:10.1248/cpb.34.999

Reference yield:

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

: 105499-99-8
(3S,4R)-3-<(1R)-(tert-butyldimethylsiloxy)ethyl>-4-<5-(p-nitrobenzyloxycarbonylamino)pentanoylthio>azetidin-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: 99 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 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