(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

Base Information

Chemical Name:(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid
CAS No.:156350-22-0
Molecular Formula:C₁₇H₂₇NO₅SSi
Molecular Weight:385.557
Hs Code.:

Synonyms:(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

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Chemical Property of (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

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Technology Process of (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

There total 6 articles about (2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 156350-22-0
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 99 percent / imidazole / dimethylformamide / 3 h / 50 °C

2: 53 mg / NaIO₄, RuCl₃ / ethyl acetate; acetonitrile; H₂O / 40 h / Ambient temperature

With 1H-imidazole; ruthenium trichloride; sodium periodate; In water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)80749-3

Reference yield:

: 146499-47-0
(2R,3R)-3-azido-2-tert-butyldimethylsiloxy-3-phenyl-1-p-toluenesulfonyloxypropane

: 156350-22-0
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 4 steps

1: 1.33 g / 5percent Pd-C, HCO₂NH₄ / methanol / 1 h / Ambient temperature

2: Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

3: 75 percent / NaH / methanol / 11 h / Ambient temperature

4: 53 mg / NaIO₄, RuCl₃ / ethyl acetate; acetonitrile; H₂O / 40 h / Ambient temperature

With dmap; ruthenium trichloride; sodium periodate; palladium on activated charcoal; ammonium formate; sodium hydride; triethylamine; In methanol; dichloromethane; water; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4020(01)80749-3

Reference yield:

: 146499-48-1
(2R,3R)-2-tert-butyldimethylsiloxy-3-phenyl-3-p-toluenesulfonylamino-1-p-toluenesulfonylpropane

: 156350-22-0
(2S,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-(toluene-4-sulfonyl)-azetidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 18 percent / NaH / methanol / 11 h / Ambient temperature

2: 99 percent / imidazole / dimethylformamide / 3 h / 50 °C

3: 53 mg / NaIO₄, RuCl₃ / ethyl acetate; acetonitrile; H₂O / 40 h / Ambient temperature

With 1H-imidazole; ruthenium trichloride; sodium periodate; sodium hydride; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4020(01)80749-3