(4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 189152-96-3
• Molecular Formula: C₂₇H₂₅N₃O₇S₂
• Molecular Weight: 567.643
• Mol file: 189152-96-3.mol

Synonyms:

Chemical Property of (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-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 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 6 articles about (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-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:

(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate (161692-28-0) + 4-(4-hydroxymethylphenyl)-2-mercaptothiazole (161681-83-0) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (189152-96-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; toluene; at 5 ℃; for 18h;

DOI:10.1016/S0968-0896(96)00273-8

Reference yield:

4-acetyl-benzoic acid (586-89-0) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (189152-96-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / bromine, aluminium chloride / diethyl ether / 3 h / Ambient temperature

2: 75 percent / ethanol / 1.) RT, 20 h, 2.) 70 deg C - 80 deg C, 30 min

3: Et₃N / tetrahydrofuran; dimethylformamide / -78 - -20 °C

4: sodium borohydride / tetrahydrofuran; dimethylformamide; H₂O / 1 h / 0 °C

5: 85 percent / methanol / 1 h / Ambient temperature

6: NaH / toluene; tetrahydrofuran / 18 h / 5 °C

With sodium tetrahydroborate; aluminium trichloride; bromine; sodium hydride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(96)00273-8

Reference yield:

4-(2-bromoacetyl)benzoic acid (20099-90-5) → (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[4-(4-hydroxymethyl-phenyl)-thiazol-2-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (189152-96-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / ethanol / 1.) RT, 20 h, 2.) 70 deg C - 80 deg C, 30 min

2: Et₃N / tetrahydrofuran; dimethylformamide / -78 - -20 °C

3: sodium borohydride / tetrahydrofuran; dimethylformamide; H₂O / 1 h / 0 °C

4: 85 percent / methanol / 1 h / Ambient temperature

5: NaH / toluene; tetrahydrofuran / 18 h / 5 °C

With sodium tetrahydroborate; sodium hydride; triethylamine; In tetrahydrofuran; methanol; ethanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0968-0896(96)00273-8

upstream raw materials:

(4R,5R,6S,8R)-p-nitrobenzyl-3-(diphenylphosphoryloxy)-4-methyl-6-(1-(trimethylsilyloxy)ethyl)-7-oxo-1-azabicyclo<3.2.0>hept-2-ene-2-carboxylate

4-(4-hydroxymethylphenyl)-2-mercaptothiazole

4-acetyl-benzoic acid

4-(2-bromoacetyl)benzoic acid