4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Base Information

Chemical Name:4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester
CAS No.:84787-59-7
Molecular Formula:C₂₀H₂₈N₂O₇Si
Molecular Weight:436.537
Hs Code.:

Synonyms:4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

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Chemical Property of 4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

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Technology Process of 4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

There total 10 articles about 4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-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:

: 77856-52-1
(S)-3-<(benzyloxycarbonyl)amino>-4-(methoxycarbonyl)butyric acid

: 84787-59-7
4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: NaBH₄

2: Ac₂O / pyridine

3: 77 percent / LDA / tetrahydrofuran / 1 h / -78 °C

4: 88 percent Turnov_. / hydrochloric acid

5: H₂, catalyst

6: Et₃N / diethyl ether / 2 h / 25 °C

7: t-BuMgCl / diethyl ether / 12 h / 25 °C

8: 1percent AcOH / methanol / 24 h / 25 °C

9: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

10: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

With chromium(VI) oxide; hydrogenchloride; sodium tetrahydroborate; tert-butylmagnesium chloride; hydrogen; acetic anhydride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; diethyl ether;
DOI:10.1021/ja00344a044

Reference yield:

: 84787-58-6
(2R,3R)-3-Amino-5-hydroxy-2-(1-hydroxy-1-methyl-ethyl)-pentanoic acid methyl ester

: 84787-59-7
4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: Et₃N / diethyl ether / 2 h / 25 °C

2: t-BuMgCl / diethyl ether / 12 h / 25 °C

3: 1percent AcOH / methanol / 24 h / 25 °C

4: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

5: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

With chromium(VI) oxide; tert-butylmagnesium chloride; acetic acid; triethylamine; 1,1'-carbonyldiimidazole; In pyridine; methanol; diethyl ether;
DOI:10.1021/ja00344a044

Reference yield:

: 84787-55-3
(3R,4R)-4-(2-Hydroxy-ethyl)-3-(1-methyl-1-trimethylsilanyloxy-ethyl)-azetidin-2-one

: 84787-59-7
4-[(2R,3R)-3-(1-Methyl-1-trimethylsilanyloxy-ethyl)-4-oxo-azetidin-2-yl]-3-oxo-butyric acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 66 percent / CrO₃ / pyridine / 12 h / 25 °C

2: 1.) carbonyl diimidazole / 1.) THF, 25 deg C, 45 min, 2.) TFH, 25 deg C, 12 h

With chromium(VI) oxide; 1,1'-carbonyldiimidazole; In pyridine;
DOI:10.1021/ja00344a044