(3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone

Base Information

• Chemical Name: (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone
• CAS No.: 91814-67-4
• Molecular Formula: C₂₄H₄₂N₂O₄Si₂
• Molecular Weight: 478.779
• Mol file: 91814-67-4.mol

Synonyms:(3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone

Chemical Property of (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone

There total 2 articles about (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-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:

(S) 1-(tert-butyldimethylsilyl)-4-<((tert-butyldimethylsilyl)oxy)methyl>-2-azetidinone (91814-59-4) → (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone (91814-67-4)

Guidance literature:

Multi-step reaction with 3 steps

2: H₂ / 10 percent Pd-C / tetrahydrofuran / 1.5 h / Ambient temperature

3: N,N'-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole / tetrahydrofuran / 2 h / Ambient temperature

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1248/cpb.32.1303

Reference yield:

(3R,4S)-3-azido-1-tert-butyldimethylsilyl-4-tert-butyldimethylsilyloxymethyl-2-azetidinone (91814-61-8) → (3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone (91814-67-4)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10 percent Pd-C / tetrahydrofuran / 1.5 h / Ambient temperature

2: N,N'-dicyclohexylcarbodiimide, 1-hydroxybenzotriazole / tetrahydrofuran / 2 h / Ambient temperature

With hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran;

DOI:10.1248/cpb.32.1303

Reference yield: 97.0%

(3R,4S)-1-tert-butyldimethylsilyl-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone (91814-67-4) → (3R,4S)-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone (91814-68-5)

Guidance literature:

With potassium fluoride; acetic acid; In methanol; at 0 ℃; for 0.25h;

DOI:10.1248/cpb.32.1303

upstream raw materials:

(S) 1-(tert-butyldimethylsilyl)-4-<((tert-butyldimethylsilyl)oxy)methyl>-2-azetidinone

(3R,4S)-3-azido-1-tert-butyldimethylsilyl-4-tert-butyldimethylsilyloxymethyl-2-azetidinone

Downstream raw materials:

(3R,4S)-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-azetidinone

(3R,4S)-4-hydroxymethyl-3-phenoxyacetamido-2-oxo-1-sulfoazetidine 3,3,6,9,9-pentamethyl-2,10-diazabicyclo<4.4.0>-1-decene salt

(3R,4S)-4-acetoxymethyl-3-phenoxyacetamido-2-oxo-1-sulfoazetidine 3,3,6,9,9-pentamethyl-2,10-diazabicyclo<4.4.0>-1-decene salt

(3R,4S)-4-tert-bytyldimethylsilyloxymethyl-3-phenoxyacetamido-2-oxo-1-sulfoazetidinone 3,3,6,9,9-pentamethyl-2,10-diazabicyclo<4.4.0>-1-decene salt