(3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one
• CAS No.: 253327-55-8
• Molecular Formula: C₂₂H₂₆INO₃Si
• Molecular Weight: 507.443
• Mol file: 253327-55-8.mol

Synonyms:(3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one

Chemical Property of (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one

There total 1 articles about (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one 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: 50.0%

benzoyl chloride (98-88-4) + (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-54-7) → (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-55-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane;

DOI:10.1016/S0960-894X(99)00522-3

Reference yield: 40.0%

7-(triethylsilyl)baccatin III (115437-21-3) + (3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-55-8) → C53H62INO13Si (253327-59-2) + C59H78INO14Si2 (253327-56-9)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 35 ℃;

DOI:10.1016/S0960-894X(99)00522-3

Reference yield:

(3R,4S)-1-Benzoyl-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-55-8) → C49H53NO14

Guidance literature:

Multi-step reaction with 6 steps

1: 40 percent / NaH / tetrahydrofuran / 0 - 35 °C

2: 63 percent / aq. t-BuOK / tetrahydrofuran / -42 - -15 °C

3: 87 percent / DCC; DMAP / toluene / 55 °C

4: Pd(OAc)2; PPh₃; AgCO₃ / acetonitrile / 60 °C

5: 76 percent / pyridine*HF

6: 85 percent / H₂ / Pd/C

With dmap; palladium diacetate; silver (II) carbonate; potassium tert-butylate; hydrogen; sodium hydride; pyridine hydrogenfluoride; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; toluene; acetonitrile; 1: Addition / 2: Hydrolysis / 3: Esterification / 4: Heck macrocyclization / 5: desilylation / 6: Catalytic hydrogenation;

DOI:10.1016/S0960-894X(99)00522-3

upstream raw materials:

benzoyl chloride

(3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one

Downstream raw materials:

C₅₃H₆₂INO₁₃Si

C₅₉H₇₈INO₁₄Si₂

C₄₉H₅₁NO₁₄

C₅₂H₇₄INO₁₃Si₂