{(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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: {(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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester
• CAS No.: 102646-18-4
• Molecular Formula: C₄₅H₅₄N₃O₆PS₂Si
• Molecular Weight: 856.132

Synonyms:

Chemical Property of {(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}-(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 {(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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

There total 8 articles about {(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}-(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: 82.0%

(3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone (102627-95-2,102681-86-7) + 2-mercapto-5-methyl-1,3,4-thiadiazole (29490-19-5) → {(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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (102646-18-4,102681-87-8)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; Ambient temperature;

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) → {(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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (102646-18-4,102681-87-8)

Guidance literature:

Multi-step reaction with 8 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: triethylamine / tetrahydrofuran / 48 h / Ambient temperature

6: m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 72 h

7: 1.) 2,6-lutidine, thionyl chloride; 2.) 2,6-lutidine / 1.) THF, -40 min, 30 min; 2.) THF, room temperature

8: 82 percent / n-butyllithium / tetrahydrofuran; hexane / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; n-butyllithium; thionyl chloride; 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;

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) → {(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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-methoxy-benzyl ester (102646-18-4,102681-87-8)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / tetrahydrofuran / 48 h / Ambient temperature

2: m-chloroperbenzoic acid, NaHCO₃ / CH₂Cl₂ / 72 h

3: 1.) 2,6-lutidine, thionyl chloride; 2.) 2,6-lutidine / 1.) THF, -40 min, 30 min; 2.) THF, room temperature

4: 82 percent / n-butyllithium / tetrahydrofuran; hexane / Ambient temperature

With 2,6-dimethylpyridine; n-butyllithium; thionyl chloride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1248/cpb.33.4382

upstream raw materials:

(3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone

2-mercapto-5-methyl-1,3,4-thiadiazole

(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

Downstream raw materials:

(3S^*,4R^*)-3-<(R^*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-2-azetidinone

{(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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-methoxy-benzyl ester

p-methoxybenzyl (5R^*,6S^*)-6-<(R^*)-1-hydroxyethyl>-2-(5-methyl-1,3,4-thiadiazol-2-yl)thiomethylcarbapen-2-em-3-carboxylate

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