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

Base Information

• Chemical Name: (3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-2-azetidinone
• CAS No.: 128971-89-1
• Molecular Formula: C₂₁H₂₅NO₄Si
• Molecular Weight: 383.519
• Mol file: 128971-89-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about (3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-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: 72.0%

lead(IV) tetraacetate (546-67-8) + (3R,4S)-3-<(tert-Butyldiphenylsilyl)oxy>-2-oxo-4-azetidinecarboxylic Acid (128971-88-0) → (3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-2-azetidinone (128971-89-1)

Guidance literature:

In acetic acid; N,N-dimethyl-formamide; at 40 - 50 ℃;

DOI:10.1021/jo00304a024

Reference yield:

(2S,3R)-Dibenzyl 2-Azido-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-84-6) → (3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-2-azetidinone (128971-89-1)

Guidance literature:

Multi-step reaction with 4 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

4: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00304a024

Reference yield:

(2S,3R)-Dibenzyl 2-Amino-3-<(tert-butyldiphenylsilyl)oxy>succinate (128971-86-8) → (3R)-4-Acetoxy-3-<(tert-butyldiphenylsilyl)oxy>-2-azetidinone (128971-89-1)

Guidance literature:

Multi-step reaction with 3 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

3: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C

With chloro-trimethyl-silane; tert-butylmagnesium chloride; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/jo00304a024

upstream raw materials:

lead(IV) tetraacetate

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

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

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

Downstream raw materials:

(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

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