(4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 157743-80-1
• Molecular Formula: C₃₇H₄₀N₂O₈Si
• Molecular Weight: 668.819
• Mol file: 157743-80-1.mol

Synonyms:(4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 17 articles about (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic 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: 93.0%

(4S,5R,6S)-4-Methyl-7-oxo-3-(9-oxo-7-trimethylsilanyloxymethyl-9H-fluoren-3-yl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (169552-95-8) → (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (157743-80-1)

Guidance literature:

With potassium phthalate; In tetrahydrofuran; for 16h; Ambient temperature; pH 4.0;

DOI:10.1021/jo980381n

Reference yield:

triethylsilyl chloride (994-30-9) → (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (157743-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / imidazole / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2: ZnBr₂ / Rh₂(C₇H₁₅CO₂)4 / CH₂Cl₂ / 1.5 h / Heating

3: Et₃N, i-Pr₂NEt / CH₂Cl₂ / 1 h / -40 °C

5: 93 percent / aq. potassium phthalate / tetrahydrofuran / 16 h / Ambient temperature; pH 4.0

With 1H-imidazole; potassium phthalate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; Rh₂(C₇H₁₅CO₂)4; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo980381n

Reference yield:

(γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester (90822-24-5) → (4S,5R,6S)-3-(7-Hydroxymethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (157743-80-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 93 percent / imidazole / tetrahydrofuran; various solvent(s) / 2 h / 20 °C

2: ZnBr₂ / Rh₂(C₇H₁₅CO₂)4 / CH₂Cl₂ / 1.5 h / Heating

3: Et₃N, i-Pr₂NEt / CH₂Cl₂ / 1 h / -40 °C

5: 93 percent / aq. potassium phthalate / tetrahydrofuran / 16 h / Ambient temperature; pH 4.0

With 1H-imidazole; potassium phthalate; triethylamine; N-ethyl-N,N-diisopropylamine; zinc dibromide; Rh₂(C₇H₁₅CO₂)4; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo980381n

upstream raw materials:

4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate

6-Bromo-2-methoxymethyl-9-fluorenone Dimethyl Ketal

(4S,5R,6S)-4-Methyl-7-oxo-3-(9-oxo-7-trimethylsilanyloxymethyl-9H-fluoren-3-yl)-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

triethylsilyl chloride

Downstream raw materials:

(4S,5R,6S)-4-Methyl-7-oxo-3-[9-oxo-7-(propane-1-sulfonyloxymethyl)-9H-fluoren-3-yl]-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4S,5R,6S)-3-(7-Iodomethyl-9-oxo-9H-fluoren-3-yl)-4-methyl-7-oxo-6-((R)-1-triethylsilanyloxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester