(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

Base Information

Chemical Name:(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester
CAS No.:131472-72-5
Molecular Formula:C₂₇H₄₄N₂O₇Si
Molecular Weight:536.741
Hs Code.:

(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

Synonyms:(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

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Chemical Property of (S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

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Technology Process of (S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

There total 6 articles about (S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester 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: 81.0%

: 131472-71-4
(2S,3R)-2-tert-Butoxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-4-oxo-butyric acid methyl ester

: 131501-48-9
Benzyl (S)-2-azetidinecarboxylate p-toluenesulfonate salt

: 131472-72-5
(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: With sodium cyanoborohydride; In methanol; for 19h; Ambient temperature;
DOI:10.1016/S0040-4039(00)97800-6

Reference yield:

: 122767-59-3
(R)-3-tert-Butoxycarbonylamino-5-hydroxymethyltetronic acid

: 131472-72-5
(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / imidazole / dimethylformamide / 20 h / Ambient temperature

2: H₂ / Rh-Al₂O₃ / ethyl acetate / 48 h / 91200.1 Torr / Ambient temperature

3: imidazole / dimethylformamide / 0 deg C, 1 h, then room temperature, 2 d

4: 90 percent / acetic acid, water / tetrahydrofuran / 12 h / Ambient temperature

5: 44 percent / Pb(OAc)4 / benzene / 1.5 h / Heating

6: 81 percent / sodium cyanoborohydride / methanol / 19 h / Ambient temperature

With 1H-imidazole; lead(IV) acetate; water; hydrogen; sodium cyanoborohydride; acetic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)97800-6

Reference yield:

: 131472-68-9
[(R)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-4-hydroxy-2-oxo-2,5-dihydro-furan-3-yl]-carbamic acid tert-butyl ester

: 131472-72-5
(S)-1-[(2S,3S)-3-tert-Butoxycarbonylamino-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxycarbonyl-propyl]-azetidine-2-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: H₂ / Rh-Al₂O₃ / ethyl acetate / 48 h / 91200.1 Torr / Ambient temperature

2: imidazole / dimethylformamide / 0 deg C, 1 h, then room temperature, 2 d

3: 90 percent / acetic acid, water / tetrahydrofuran / 12 h / Ambient temperature

4: 44 percent / Pb(OAc)4 / benzene / 1.5 h / Heating

5: 81 percent / sodium cyanoborohydride / methanol / 19 h / Ambient temperature

With 1H-imidazole; lead(IV) acetate; water; hydrogen; sodium cyanoborohydride; acetic acid; rhodium on alumina; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; benzene;
DOI:10.1016/S0040-4039(00)97800-6