4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate
• CAS No.: 186525-22-4
• Molecular Formula: C₂₄H₃₁NO₅SSi
• Molecular Weight: 473.665

Synonyms:4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate

Chemical Property of 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate

Chemical Property:

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Technology Process of 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate

There total 8 articles about 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-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: 52.0%

4-methoxybenzyl 2-[(3S,4R)-3-[(1R)-1-(trimethylsilyloxy)ethyl]-4-[2-oxo-2-(2,5-dihydrothiophen-3-yl)ethyl]azetidin-2-on-1-yl]-2-tributylphosphoranylidene acetate → 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate (186525-22-4)

Guidance literature:

In toluene; for 1h; Heating;

DOI:10.7164/antibiotics.49.1258

Reference yield:

4-methoxybenzyl glyoxylate (64370-70-3) → 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate (186525-22-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: benzene / 16 h / 20 °C

2.1: thionyl chloride; 2,6-lutidine / tetrahydrofuran / 0.33 h / -10 °C

3.1: dioxane / 20 °C

3.2: 2,6-lutidine / dioxane / 3.5 h

4.1: hydrochloric acid; water / methanol / 3 h / 20 °C

5.1: 97 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

6.1: 52 percent / toluene / 1 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; thionyl chloride; water; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; benzene; 1.1: Addition / 2.1: Substitution / 3.1: Alkylation / 3.2: Dehydrochlorination / 4.1: desilylation / 5.1: silylation / 6.1: Wittig reaction;

DOI:10.7164/antibiotics.49.1258

Reference yield:

3-acetyl-2,5-dihydrothiophene (93198-78-8) → 4-methoxybenzyl (5R,6S)-6-[(1R)-1-(trimethylsilyloxy)ethyl]-2-(2,5-dihydrothiophen-3-yl)carbapen-2-em-3-carboxylate (186525-22-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / CH₂Cl₂ / 1.5 h / 0 °C

2.1: zinc chloride / CH₂Cl₂; diethyl ether / 16 h / 20 °C

2.2: pyridinium p-toluenesulphonate; water / tetrahydrofuran / 2 h / 20 °C

3.1: benzene / 16 h / 20 °C

4.1: thionyl chloride; 2,6-lutidine / tetrahydrofuran / 0.33 h / -10 °C

5.1: dioxane / 20 °C

5.2: 2,6-lutidine / dioxane / 3.5 h

6.1: hydrochloric acid; water / methanol / 3 h / 20 °C

7.1: 97 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

8.1: 52 percent / toluene / 1 h / Heating

With 2,6-dimethylpyridine; hydrogenchloride; thionyl chloride; water; triethylamine; zinc(II) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; toluene; benzene; 1.1: silylation / 2.1: Condensation / 2.2: desilylation / 3.1: Addition / 4.1: Substitution / 5.1: Alkylation / 5.2: Dehydrochlorination / 6.1: desilylation / 7.1: silylation / 8.1: Wittig reaction;

DOI:10.7164/antibiotics.49.1258

upstream raw materials:

4-methoxybenzyl glyoxylate

3-acetyl-2,5-dihydrothiophene

1-(2,5-dihydrothiophen-3-yl)-1-(t-butyldimethylsilyloxy)ethene

Downstream raw materials:

4-methoxybenzyl (5R,6S)-6-[(1R)-1-trimethylsilyloxyethyl]-2-(2,5-dihydrothiophen-3-yl-1,1-dioxide)carbapen-2-em-3-carboxylate

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