[(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

Base Information

• Chemical Name: [(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
• CAS No.: 102990-76-1
• Molecular Formula: C₃₈H₃₆NO₈P
• Molecular Weight: 665.679

Synonyms:

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 4 articles about [(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 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:

(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) → [(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)

Guidance literature:

Multi-step reaction with 5 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

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;

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) → [(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)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1248/cpb.33.4361

Reference yield:

(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 (84830-26-2,84848-69-1) → [(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)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / acetic acid, tetraethylammonium fluoride dihydrate / tetrahydrofuran / 2 h / Ambient temperature

2: triethylamine / tetrahydrofuran / Ambient temperature

3: 98 percent / thionyl chloride, 2,6-lutidine / tetrahydrofuran / 1.5 h / -20 °C

4: 68 percent / 2,6-lutidine / dioxane / Ambient temperature

With 2,6-dimethylpyridine; thionyl chloride; tetraethylammonium fluoride; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane;

DOI:10.1248/cpb.33.4361

upstream raw materials:

(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

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

Downstream raw materials:

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

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

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