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

Base Information

• Chemical Name: (3S^*,4R^*)-3-<(R^*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-2-azetidinone
• CAS No.: 102627-96-3
• Molecular Formula: C₃₉H₃₈N₃O₆PS₂
• Molecular Weight: 739.853

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

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

Chemical Property:

Purity/Quality:

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

There total 10 articles about (3S^*,4R^*)-3-<(R^*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-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: 79.0%

{(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 (102646-19-5) → (3S*,4R*)-3-<(R*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-2-azetidinone (102627-96-3)

Guidance literature:

With hydrogenchloride; In methanol; acetonitrile; for 1h; 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) → (3S*,4R*)-3-<(R*)-1-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-2-azetidinone (102627-96-3)

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: 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

9: 95 percent / trifluoroacetic anhydride, dimethylsulfoxide / CH₂Cl₂ / 0.5 h / -70 °C

10: 79 percent / hydrochloric acid / methanol; acetonitrile / 1 h / Ambient temperature

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; sodium periodate; n-butyllithium; thionyl chloride; tetraethylammonium fluoride; sodium hydrogencarbonate; potassium tri-sec-butyl-borohydride; acetic acid; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

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-hydroxyethyl>-1-(p-methoxybenzyloxycarbonyl)triphenylphosphoranylidenemethyl-4-<3-(5-methyl-1,3,4-thiadiazol-2-ylthio)-2-oxopropyl>-2-azetidinone (102627-96-3)

Guidance literature:

Multi-step reaction with 6 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

5: 95 percent / trifluoroacetic anhydride, dimethylsulfoxide / CH₂Cl₂ / 0.5 h / -70 °C

6: 79 percent / hydrochloric acid / methanol; acetonitrile / 1 h / Ambient temperature

With 2,6-dimethylpyridine; hydrogenchloride; n-butyllithium; thionyl chloride; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1248/cpb.33.4382

upstream raw materials:

{(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^*)-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

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