(5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 80926-64-3
• Molecular Formula: C₂₁H₂₈N₂O₆S₂Si
• Molecular Weight: 496.681
• Mol file: 80926-64-3.mol

Synonyms:(5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property of (5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester

There total 12 articles about (5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-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: 90.0%

4-Nitrobenzyl 3,3-di(acetylthio)-2-[(3S,4R)-4-chloro-3-(1'(R)-{dimethyl-{2-methylprop-2-yl}silyloxy}ethyl)-2-azetidinon-1-yl]propenoate (88816-47-1) → (5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-7-oxo-3-thioxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester (80926-64-3)

Guidance literature:

With 1H-imidazole; In 1,4-dioxane; water; at 20 ℃;

DOI:10.1039/c39830001006

Reference yield:

4-nitrobenzyl bromoacetate (16869-24-2) → racemic p-nitrobenzyl (3S,5R,6S)-6-((R)-1-(t-butyl-dimethylsilyloxy)ethyl)-2-thioxopenam-3-carboxylate (80926-64-3,81779-81-9,83807-49-2,85001-69-0,88035-36-3,93603-72-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / dicyclohexyl-18-crown-6, KOH / benzene / 4.5 h / Ambient temperature

2: AgNO₃, pyridine / methanol / 0.5 h / 0 °C

3: 64 percent / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

4: 1) Li hexamethyldisilazid, 1,3-dimethyl-2-imidazolidone; 2) 2N HCl / 1) THF, hexane, -78 deg C

With pyridine; 1,3-dimethyl-2-imidazolidinone; hydrogenchloride; perhydrodibenzo-18-crown-6; potassium hydroxide; silver nitrate; lithium hexamethyldisilazane; In methanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)92144-1

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → racemic p-nitrobenzyl (3S,5R,6S)-6-((R)-1-(t-butyl-dimethylsilyloxy)ethyl)-2-thioxopenam-3-carboxylate (80926-64-3,81779-81-9,83807-49-2,85001-69-0,88035-36-3,93603-72-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / imidazole / dimethylformamide / 24 h / Ambient temperature

2: 68 percent / dicyclohexyl-18-crown-6, KOH / benzene / 4.5 h / Ambient temperature

3: AgNO₃, pyridine / methanol / 0.5 h / 0 °C

4: 64 percent / pyridine / CH₂Cl₂ / 0.33 h / 0 °C

5: 1) Li hexamethyldisilazid, 1,3-dimethyl-2-imidazolidone; 2) 2N HCl / 1) THF, hexane, -78 deg C

With pyridine; 1H-imidazole; 1,3-dimethyl-2-imidazolidinone; hydrogenchloride; perhydrodibenzo-18-crown-6; potassium hydroxide; silver nitrate; lithium hexamethyldisilazane; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)92144-1

upstream raw materials:

racemic (3S,4R)-1-(p-nitrobenzyloxycarbonyl)methyl-3-<((R)-1-t-butyldimethylsilyloxy)-ethyl>-4-phenoxy(thiocarbonyl)thio-2-azetidinone

4-nitrobenzyl bromoacetate

tert-butyldimethylsilyl chloride

racemic (3S,4R)-3-((R)-1-hydroxyethyl)-4-triphenylmethylthio-2-azetidinone

Downstream raw materials:

(5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-3-Cyanomethylsulfanyl-6-((R)-1-hydroxy-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(5R,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-cyanomethylsulfanyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester