2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-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-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester
• CAS No.: 90488-91-8
• Molecular Formula: C₄₃H₅₄N₃O₇PS₂Si
• Molecular Weight: 848.109

Synonyms:

Chemical Property of 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ⁵-phosphanylidene)-acetoxymethyl ester

There total 10 articles about 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-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)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[2-hydroxy-3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (90488-91-8)

Guidance literature:

With jones' reagent; In acetone; for 0.5h; ice-cooling;

DOI:10.1248/cpb.33.4382

Reference yield:

(3S*,4R*)-4-allyl-1-tert-butyldimethylsilyl-3-(1,2-dihydroxy-2-propyl)-2-azetidinone (84829-77-6,84848-56-6,102680-60-4) → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (90488-91-8)

Guidance literature:

Multi-step reaction with 10 steps

1: sodium metaperiodate / tetrahydrofuran; H₂O / 0.25 h / Ambient temperature

2: 47 percent / K-selectride / tetrahydrofuran / 0.5 h / Ambient temperature

3: imidazole / dimethylformamide / Ambient temperature

4: tetraethylammonium fluoride dihydrate, acetic acid / tetrahydrofuran / 1 h / Ambient temperature

5: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, ice-cooling, 50 min

6: 98 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 48 h / Ambient temperature

7: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -30 °C

8: 2,6-lutidine / tetrahydrofuran / Ambient temperature

9: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / Ambient temperature

10: 60 percent / Jones' reagent / acetone / 0.5 h / ice-cooling

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; n-butyllithium; thionyl chloride; jones' reagent; 4 A molecular sieve; tetraethylammonium fluoride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.33.4382

Reference yield:

(3S*,4R*)-4-allyl-3-<(R*)-1-tert-butyldimethylsiloxyethyl>-2-azetidinone (74614-73-6,80433-47-2,90580-72-6,92936-62-4,139492-84-5) → 2,2-Dimethyl-propionic acid 2-{(2R,3S)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[3-(5-methyl-[1,3,4]thiadiazol-2-ylsulfanyl)-2-oxo-propyl]-4-oxo-azetidin-1-yl}-2-(triphenyl-λ5-phosphanylidene)-acetoxymethyl ester (90488-91-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) triethylamine, molecular sieves 4A / 1.) THF, room temperature; 2.) DMF, ice-cooling, 50 min

2: 98 percent / m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 48 h / Ambient temperature

3: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.5 h / -30 °C

4: 2,6-lutidine / tetrahydrofuran / Ambient temperature

5: n-butyllithium / hexane; tetrahydrofuran / 0.17 h / Ambient temperature

6: 60 percent / Jones' reagent / acetone / 0.5 h / ice-cooling

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

DOI:10.1248/cpb.33.4382

upstream raw materials:

(3S^*,4R^*)-4-allyl-1-tert-butyldimethylsilyl-3-(1,2-dihydroxy-2-propyl)-2-azetidinone

(3S^*,4R^*)-4-allyl-3-<(R^*)-1-tert-butyldimethylsiloxyethyl>-2-azetidinone

(3S,4R)-3-Acetyl-4-allyl-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one

(3S^*,4R^*)-4-allyl-1-tert-butyldimethylsilyl-3-<(R^*)-1-hydroxyethyl>-2-azetidinone

Downstream raw materials:

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

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