p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate

Base Information

• Chemical Name: p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate
• CAS No.: 97129-03-8
• Molecular Formula: C₂₂H₂₁N₃O₇S₃
• Molecular Weight: 535.623

Synonyms:

Chemical Property of p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate

There total 16 articles about p-methoxybenzyl (5R^*,6S^*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate 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:

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (102991-09-3,103065-69-6) → p-methoxybenzyl (5R*,6S*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate (97129-03-8,103065-78-7,103065-79-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-lutidine, thionyl bromide / tetrahydrofuran / 0.5 h / -30 °C

2: 2,6-lutidine / dioxane / 10 h / Ambient temperature

3: 1.) AgNO₃; 2.) pyridine / 1.) THF/water, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

4: 76 percent / toluene / 1.5 h / 60 °C

5: tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; tetrabutylammomium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1248/cpb.33.4371

Reference yield:

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (102991-09-3,103065-69-6) → p-methoxybenzyl (5R*,6S*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate (97129-03-8,103065-78-7,103065-79-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,6-lutidine, thionyl bromide / tetrahydrofuran / 0.5 h / -30 °C

2: 2,6-lutidine / dioxane / 10 h / Ambient temperature

3: 1.) AgNO₃; 2.) pyridine / 1.) THF/water, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

4: toluene / 1.5 h / 60 °C

5: tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; dibromo sulfoxide; silver nitrate; tetrabutylammomium bromide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1248/cpb.33.4371

Reference yield:

Bromo-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester (102991-10-6,103065-70-9) → p-methoxybenzyl (5R*,6S*)-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-<(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl>penem-3-cerboxylate (97129-03-8,103065-78-7,103065-79-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 2,6-lutidine / dioxane / 10 h / Ambient temperature

2: 1.) AgNO₃; 2.) pyridine / 1.) THF/water, ice-cooling, 3 h; 2.) CH₂Cl₂, -40 degC, 1 h

3: 76 percent / toluene / 1.5 h / 60 °C

4: tetra-n-butylammonium bromide / CH₂Cl₂; H₂O / 2 h / Ambient temperature

With pyridine; 2,6-dimethylpyridine; silver nitrate; tetrabutylammomium bromide; In 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1248/cpb.33.4371

upstream raw materials:

sodium salt of 5-mercapto-2-methyl-1,3,4-thiadiazole

p-methoxybenzyl (5R^*,6S^*)-2-chloromethyl-6-(4-methyl-2-oxo-1,3-dioxolan-4-yl)penem-3-carboxylate

Hydroxy-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester

Bromo-[(3R,4S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-tritylsulfanyl-azetidin-1-yl]-acetic acid 4-methoxy-benzyl ester

Downstream raw materials:

p-methoxybenzyl 6-<(E)-1-(hydroxymethyl)ethylidene>-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylpenem-3-carboxylate

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