(3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid

Base Information

• Chemical Name: (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid
• CAS No.: 128971-88-0
• Molecular Formula: C₂₀H₂₃NO₄Si
• Molecular Weight: 369.492
• Mol file: 128971-88-0.mol

Synonyms:(3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid

Chemical Property of (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid

There total 3 articles about (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic 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: 99.0%

(3R,4S)-Benzyl 3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylate (128971-87-9) → (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid (128971-88-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00304a024

Reference yield:

(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-84-6) → (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid (128971-88-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / PPh₃ / tetrahydrofuran; H₂O / 18 h / 60 °C

2: 1) Me₃SiCl, Et₃N, 2) t-BuMgCl / 1) Et₂O, 0 deg C, 1 h, 2) Et₂O, room temp., 18 h

3: 99 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / Ambient temperature

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; water;

DOI:10.1021/jo00304a024

Reference yield:

(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-86-8) → (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid (128971-88-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) Me₃SiCl, Et₃N, 2) t-BuMgCl / 1) Et₂O, 0 deg C, 1 h, 2) Et₂O, room temp., 18 h

2: 99 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / Ambient temperature

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1021/jo00304a024

upstream raw materials:

(3R,4S)-Benzyl 3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylate

(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate

(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate

Downstream raw materials:

(3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-2-azetidinone

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-buten-2-yl)thio>-2-azetidinone

(3S,4R)-3-<(tert-Butyldiphenylsilyl)oxy>-1-<(2,3-dimethyl-2-butyl)dimethylsilyl>-4-<(2-methyl-3-oxo-2-propyl)thio>-2-azetidinone