2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester
• CAS No.: 102990-90-9
• Molecular Formula: C₃₈H₄₀N₅O₉PS
• Molecular Weight: 773.803

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

Chemical Property:

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Safty Information:

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Technology Process of 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

There total 11 articles about 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl 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: 60.0%

2,2-Dimethyl-propionic acid 2-[(2R,3S)-2-[2-hydroxy-3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-propyl]-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-89-6,103065-49-2) → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-90-9)

Guidance literature:

With jones' reagent; In acetone; for 1h; ice-cooling;

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) → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((S)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-90-9)

Guidance literature:

Multi-step reaction with 6 steps

1: m-chloroperbenzoic acid / CH₂Cl₂ / 48 h / Ambient temperature

2: acetic acid / BF₃-etherate / CH₂Cl₂ / Ambient temperature

3: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, 10 min, ice-cooling, 5 min, room temperature

4: 1.) thionyl chloride, 2,6-lutidine; 2.) 2,6-lutidine / 1.) THF, -20 degC, 30 min; 2.) dioxane, room temperature

5: n-butyllithium / hexane; tetrahydrofuran / Ambient temperature

6: 60 percent / Jones' reagent / acetone / 1 h / ice-cooling

With 2,6-dimethylpyridine; n-butyllithium; thionyl chloride; jones' reagent; 4 A molecular sieve; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1248/cpb.33.4361

Reference yield:

(3S*,4R*)-1-tert-butyldimethylsilyl-4-(2,3-epoxypropyl)-3-<(4R*)-4-methyl-2-oxo-1,3-dioxolan-4-yl>-2-azetidinone (102990-80-7,103065-36-7,103065-43-6,103065-44-7) → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-[3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (102990-90-9)

Guidance literature:

Multi-step reaction with 5 steps

1: acetic acid / BF₃-etherate / CH₂Cl₂ / Ambient temperature

2: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, 10 min, ice-cooling, 5 min, room temperature

3: 1.) thionyl chloride, 2,6-lutidine; 2.) 2,6-lutidine / 1.) THF, -20 degC, 30 min; 2.) dioxane, room temperature

4: n-butyllithium / hexane; tetrahydrofuran / Ambient temperature

5: Jones' reagent / acetone / 1 h / ice-cooling

With 2,6-dimethylpyridine; n-butyllithium; thionyl chloride; jones' reagent; 4 A molecular sieve; acetic acid; triethylamine; boron trifluoride diethyl etherate; In tetrahydrofuran; hexane; dichloromethane; acetone;

DOI:10.1248/cpb.33.4361

upstream raw materials:

2,2-Dimethyl-propionic acid 2-[(2R,3S)-2-[2-hydroxy-3-(1-methyl-1H-tetrazol-5-ylsulfanyl)-propyl]-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-4-oxo-azetidin-1-yl]-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

2,2-Dimethyl-propionic acid 2-[(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxiranylmethyl-4-oxo-azetidin-1-yl]-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

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

2,2-Dimethyl-propionic acid 2-hydroxy-2-[(2R,3S)-3-((R)-4-methyl-2-oxo-[1,3]dioxolan-4-yl)-2-oxiranylmethyl-4-oxo-azetidin-1-yl]-acetoxymethyl ester

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