p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate

Base Information

• Chemical Name: p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate
• CAS No.: 102990-77-2
• Molecular Formula: C₂₀H₂₁NO₇
• Molecular Weight: 387.389

Synonyms:p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate

Chemical Property of p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate

Chemical Property:

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Technology Process of p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate

There total 6 articles about p-methoxybenzyl (5R^*,6S^*)-2-methyl-6-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-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: 69.0%

[(3S,4R)-3-((R)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-(2-oxo-propyl)-azetidin-1-yl]-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (102990-76-1) → p-methoxybenzyl (5R*,6S*)-2-methyl-6-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate (102990-77-2)

Guidance literature:

In toluene; for 3.5h; Heating;

DOI:10.1248/cpb.33.4361

Reference yield:

(3S*,4R*)-4-allyl-1-tert-butyldimethylsilyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone (84829-80-1,84848-59-9,91177-16-1) → p-methoxybenzyl (5R*,6S*)-2-methyl-6-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate (102990-77-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 86 percent / mercuric acetate, coprous chloride dihydrate / palladium chloride / methanol / 1 h / 60 °C

2: 83 percent / acetic acid, tetraethylammonium fluoride dihydrate / tetrahydrofuran / 2 h / Ambient temperature

3: triethylamine / tetrahydrofuran / Ambient temperature

4: 98 percent / thionyl chloride, 2,6-lutidine / tetrahydrofuran / 1.5 h / -20 °C

5: 68 percent / 2,6-lutidine / dioxane / Ambient temperature

6: 69 percent / toluene / 3.5 h / Heating

With 2,6-dimethylpyridine; thionyl chloride; mercury(II) diacetate; tetraethylammonium fluoride; acetic acid; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; 1,4-dioxane; methanol; toluene;

DOI:10.1248/cpb.33.4361

Reference yield:

(3S*,4R*)-3-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>-4-(2-oxopropyl)-2-azetidinone (84829-83-4,84848-62-4) → p-methoxybenzyl (5R*,6S*)-2-methyl-6-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>carbapen-2-em-3-carboxylate (102990-77-2)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / tetrahydrofuran / Ambient temperature

2: 98 percent / thionyl chloride, 2,6-lutidine / tetrahydrofuran / 1.5 h / -20 °C

3: 68 percent / 2,6-lutidine / dioxane / Ambient temperature

4: 69 percent / toluene / 3.5 h / Heating

With 2,6-dimethylpyridine; thionyl chloride; triethylamine; In tetrahydrofuran; 1,4-dioxane; toluene;

DOI:10.1248/cpb.33.4361

upstream raw materials:

[(3S,4R)-3-((R)-4-Methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxo-4-(2-oxo-propyl)-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

(3S^*,4R^*)-4-allyl-1-tert-butyldimethylsilyl-3-(4-methyl-2-oxo-1,3-dioxolan-4-yl)-2-azetidinone

(3S^*,4R^*)-3-<(4R^*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>-4-(2-oxopropyl)-2-azetidinone

(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-4-(2-oxo-propyl)-azetidin-2-one

Downstream raw materials:

p-methoxybenzyl 6-<(E)-1-(hydroxymethyl)ethylidene>-2-methylcarbapen-2-em-3-carboxylate

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