p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate

Base Information

• Chemical Name: p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate
• CAS No.: 105420-65-3
• Molecular Formula: C₁₇H₁₈N₂O₆S
• Molecular Weight: 378.406
• Mol file: 105420-65-3.mol

Synonyms:p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate

Chemical Property of p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate

There total 12 articles about p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-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: 95.0%

dl-p-nitrobenzyl (5R*,6S*)-6-<(1S*)-(tert-butyldimethylsiloxy)ethyl>-2-(4-p-nitrobenzyloxycarbonylaminobutan-1-yl)-2-penem-3-carboxylate (81225-37-8,81225-38-9,85579-78-8,85579-79-9,105498-48-4) → p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate (105420-65-3)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 16h; Ambient temperature;

DOI:10.1248/cpb.34.999

Reference yield:

methyl 6-α-bromo-6-β-<(1R)-hydroxyethyl>penicillanate (80629-46-5) → p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate (105420-65-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 86 percent / 1.) silver acetate, activated zinc powder; 2.) allyl bromide / 1.) acetic acid, 110-120 deg C, 1 min; 2.) methanol, -20 deg C, 20 min

2: 51 percent / imidazole / dimethylformamide

3: 90 percent / mercuric acetate / 1.5 h / 90 °C

4: 83 percent / KMnO₄ in water / acetic acid; acetone / 3 h / Ambient temperature

5: 98 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 h

6: 86 percent / benzene / 2 h / Heating

7: 2,6-lutidine, SOCl₂ / tetrahydrofuran / 1 h / -20 °C

8: 2,6-lutidine / dioxane / 1 h / -50 - 60 °C

9: 46 percent / hydroquinone / toluene / 20 h / 90 - 100 °C

10: 95 percent / acetic acid, tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 16 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; sodium hydroxide; potassium permanganate; thionyl chloride; mercury(II) diacetate; tetrabutyl ammonium fluoride; silver(I) acetate; acetic acid; allyl bromide; hydroquinone; zinc; In tetrahydrofuran; 1,4-dioxane; acetic acid; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1248/cpb.34.999

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → p-nitrobenzyl (5R,6S)-6-<(1R)-hydroxyethyl>-2-ethyl-2-penem-3-carboxylate (105420-65-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / 1.) 1 N NaOH / 0 °C / 1.) 20 min; 2.) dioxane, 1.5 h

2: 86 percent / benzene / 2 h / Heating

3: 2,6-lutidine, SOCl₂ / tetrahydrofuran / 1 h / -20 °C

4: 2,6-lutidine / dioxane / 1 h / -50 - 60 °C

5: 46 percent / hydroquinone / toluene / 20 h / 90 - 100 °C

6: 95 percent / acetic acid, tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 16 h / Ambient temperature

With 2,6-dimethylpyridine; sodium hydroxide; thionyl chloride; tetrabutyl ammonium fluoride; acetic acid; hydroquinone; In tetrahydrofuran; 1,4-dioxane; toluene; benzene;

DOI:10.1248/cpb.34.999

upstream raw materials:

dl-p-nitrobenzyl (5R*,6S*)-6-<(1S*)-(tert-butyldimethylsiloxy)ethyl>-2-(4-p-nitrobenzyloxycarbonylaminobutan-1-yl)-2-penem-3-carboxylate

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

methyl (3S,5R,6S)-6-<(1R)-(tert-butyldimethylsiloxy)ethyl>penicillanate

p-nitrobenzyl glyoxylate

Refernces