(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

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Chemical Name:(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one
CAS No.:612546-49-3
Molecular Formula:C₂₇H₄₉NO₅SSi₂
Molecular Weight:555.927
Hs Code.:

Synonyms:(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

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Chemical Property of (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

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Technology Process of (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

There total 12 articles about (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-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: 90.0%

: 612546-53-9
(2S,3R,4R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-3-(toluene-4-sulfonylamino)-pentanoic acid amide

: 612546-49-3
(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

Guidance literature:: With dmap; di-tert-butyl dicarbonate; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1055/s-2003-39910

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 612546-49-3
(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: methanol / 20 °C

2: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

3: hexamethylphosphoric acid triamide / 20 °C

4: 91 percent / DIBAL / CH₂Cl₂ / -78 °C

5: 89 percent / H₂O₂; NH₄OH / ethanol / 20 °C

6: 87 percent / imidazole / dimethylformamide / 20 °C

7: 90 percent / t-Boc₂O; DMAP; Et₃N / CH₂Cl₂ / 20 °C

With 1H-imidazole; dmap; ammonium hydroxide; di-tert-butyl dicarbonate; dihydrogen peroxide; diisobutylaluminium hydride; triethylamine; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1055/s-2003-39910

Reference yield:

: 612546-37-9
(Z)-(2R,5R)-6-Methoxymethoxy-5-methyl-hex-3-en-2-ol

: 612546-49-3
(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-1-(toluene-4-sulfonyl)-azetidin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: DBU / acetonitrile / 0 °C

2.1: IBr; DBU / CH₂Cl₂; acetonitrile / -78 - -50 °C

3.1: aq. HCl / methanol / 20 °C

3.2: NaHCO₃ / methanol / 20 °C

4.1: methanol / 20 °C

5.1: 94 percent / DMAP; Et₃N / CH₂Cl₂ / 0 °C

6.1: hexamethylphosphoric acid triamide / 20 °C

7.1: 91 percent / DIBAL / CH₂Cl₂ / -78 °C

8.1: 89 percent / H₂O₂; NH₄OH / ethanol / 20 °C

9.1: 87 percent / imidazole / dimethylformamide / 20 °C

10.1: 90 percent / t-Boc₂O; DMAP; Et₃N / CH₂Cl₂ / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; ammonium hydroxide; di-tert-butyl dicarbonate; dihydrogen peroxide; iodine(I) bromide; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1055/s-2003-39910