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

Base Information

• Chemical Name: (3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone
• CAS No.: 102627-95-2
• Molecular Formula: C₄₂H₅₀NO₆PSi
• Molecular Weight: 723.921

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3S^*,4R^*)-3-<(R^*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone 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-(1,2-dihydroxy-2-propyl)-2-azetidinone (84829-77-6,84848-56-6,102680-60-4) → (3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone (102627-95-2,102681-86-7)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; 2,6-dimethylpyridine; sodium periodate; thionyl chloride; tetraethylammonium fluoride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 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) → (3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone (102627-95-2,102681-86-7)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1248/cpb.33.4382

Reference yield:

(3S,4R)-3-Acetyl-4-allyl-1-(tert-butyl-dimethyl-silanyl)-azetidin-2-one (77526-93-3,78130-13-9) → (3S*,4R*)-3-<(R*)-1-tert-butyldimethylsilyloxyethyl>-4-(2,3-epoxypropyl)-1-(p-methoxybenzyloxycarbonyl)-triphenylphosphoranylidenemethyl-2-azetidinone (102627-95-2,102681-86-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 47 percent / K-selectride / tetrahydrofuran / 0.5 h / Ambient temperature

2: imidazole / dimethylformamide / Ambient temperature

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

4: triethylamine / tetrahydrofuran / 48 h / Ambient temperature

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

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

With 1H-imidazole; 2,6-dimethylpyridine; thionyl chloride; tetraethylammonium fluoride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; acetic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4382

upstream raw materials:

{(2S,3R)-3-[(S)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-oxiranylmethyl-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-methoxy-benzyl ester

(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

Downstream raw materials:

{(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

{(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

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

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

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