p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate
• CAS No.: 85254-00-8
• Molecular Formula: C₂₁H₃₀N₂O₆SSi
• Molecular Weight: 466.63
• Mol file: 85254-00-8.mol

Synonyms:p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property of p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate

There total 40 articles about p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate 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: 36.0%

p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate (85253-99-2,107983-05-1,107984-12-3) → p-nitrobenzyl (2S,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85281-74-9) + p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85254-00-8)

Guidance literature:

With hydrogen sulfide; triethylamine; In dichloromethane; at 0 ℃; for 2h;

DOI:10.1246/bcsj.59.1887

Reference yield:

benzyl (2S,5R,6R)-6-<(R)-1-hydroxyethyl>penicillanate (62263-79-0) → p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85254-00-8)

Guidance literature:

Multi-step reaction with 15 steps

1: imidazole / dimethylformamide / 20 h / Ambient temperature

2: m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

3: 1,5-diazabicyclo<4.3.0>non-5-ene / CH₂Cl₂ / 1 h / 20 - 25 °C

4: potassium t-butoxide / tetrahydrofuran; dimethylformamide / 0.5 h

5: 94 percent / KMnO₄, acetic acid / acetone; H₂O / 16 h

6: 89 percent / tetrabutylammonium bromide / benzene; H₂O / 24 h

7: 85 percent / 30percent aq. H₂O₂, 0.5M Na₂CO₃ / H₂O; acetone / 0.5 h / Ambient temperature

8: NaOH / ethanol; H₂O / 1 h / 50 °C

9: ethyl acetate; diethyl ether

10: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

11: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

12: 95 percent / NaI / acetone / 7 h / 60 °C

13: 67 percent / benzene / 10 h / Heating

14: thionyl chloride, 2,6-lutidine / tetrahydrofuran / 0.33 h / -40 °C

15: 36 percent / H₂S, triethylamine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; potassium permanganate; thionyl chloride; hydrogen sulfide; potassium tert-butylate; dihydrogen peroxide; sodium carbonate; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; DBN; tetrabutylammomium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1246/bcsj.59.1887

Reference yield:

(3S,4R)-3-<(R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-(methylsulfonyl)-2-azetidinone (80813-18-9) → p-nitrobenzyl (2R,5S,6S)-6-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-7-oxo-3-thia-1-azabicyclo<3.2.0>heptane-2-carboxylate (85254-00-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 89 percent / tetrabutylammonium bromide / benzene; H₂O / 24 h

2: 85 percent / 30percent aq. H₂O₂, 0.5M Na₂CO₃ / H₂O; acetone / 0.5 h / Ambient temperature

3: NaOH / ethanol; H₂O / 1 h / 50 °C

4: ethyl acetate; diethyl ether

5: 78 percent / NaBH₄ / H₂O; tetrahydrofuran / 0.25 h / 0 °C

6: 68 percent / pyridine / tetrahydrofuran; CH₂Cl₂

7: 95 percent / NaI / acetone / 7 h / 60 °C

8: 67 percent / benzene / 10 h / Heating

9: thionyl chloride, 2,6-lutidine / tetrahydrofuran / 0.33 h / -40 °C

10: 36 percent / H₂S, triethylamine / CH₂Cl₂ / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; sodium hydroxide; sodium tetrahydroborate; thionyl chloride; hydrogen sulfide; dihydrogen peroxide; sodium carbonate; triethylamine; sodium iodide; tetrabutylammomium bromide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; acetone; benzene;

DOI:10.1246/bcsj.59.1887

upstream raw materials:

p-nitrobenzyl 2-<(3S,4S)-3-<(R)-1-(t-butyldimethylsilyloxy)ethyl>-4-iodomethyl-2-oxo-1-azetidinyl>-2-chloroacetate

(3S,4R)-3-<(R)-1-(tert-Butyldimethylsiloxy)ethyl>-4-(methylsulfonyl)-2-azetidinone

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one

(3S,4S)-3-<(R)-1'-(dimethyl-t-butylsilyloxy)ethyl>-4-oxoazetidine-2-carboxylic acid

Downstream raw materials:

(2R,6S)-6-((R)-1-Hydroxy-ethyl)-7-oxo-3-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester