(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

Base Information

Chemical Name:(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone
CAS No.:138481-24-0
Molecular Formula:C₁₉H₃₀ClNO₆SSi
Molecular Weight:464.055
Hs Code.:

Synonyms:(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

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

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Chemical Property of (3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

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Technology Process of (3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

There total 5 articles about (3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone 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: 76.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 138481-23-9
(3S,4S)-3-chloro-4-<(S)-1-hydroxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-2-azetidinone

: 138481-24-0
(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 0.333333h; Ambient temperature;
DOI:10.1248/cpb.39.2212

Reference yield:

: 138481-20-6
(S)-1-(tert-butyldimethylsilyl)oxy-3-(p-toluenesulfonyl)oxy-2-propanol

: 138481-24-0
(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / zinc acetate dihydrate / benzene; toluene / 5.5 h / Heating; azeotropic removal of water

2: hydrazine hydrate / ethanol / 0.67 h / 0 °C

3: acetic acid / ethanol / 1.) 0 deg C, 10 min, 2.) r.t., 1.4 h

4: 1.) concd. HCl, 2.) KNO₂ / 1.) ethanol, -50 deg C, 2.) a) -15 deg C, b) to 10 deg C within 0.5 h

5: 76 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium nitrite; zinc diacetate; hydrazine hydrate; acetic acid; In ethanol; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1248/cpb.39.2212

Reference yield:

: 138481-22-8
(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-phthalimido-2-azetidinone

: 138481-24-0
(3S,4S)-4-<(S)-1-(tert-butyldimethylsilyl)oxymethyl-2-<(p-toluenesulfonyl)oxy>ethoxy>-3-chloro-2-azetidinone

Guidance literature:: Multi-step reaction with 4 steps

1: hydrazine hydrate / ethanol / 0.67 h / 0 °C

2: acetic acid / ethanol / 1.) 0 deg C, 10 min, 2.) r.t., 1.4 h

3: 1.) concd. HCl, 2.) KNO₂ / 1.) ethanol, -50 deg C, 2.) a) -15 deg C, b) to 10 deg C within 0.5 h

4: 76 percent / imidazole / dimethylformamide / 0.33 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; potassium nitrite; hydrazine hydrate; acetic acid; In ethanol; N,N-dimethyl-formamide;
DOI:10.1248/cpb.39.2212