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

Base Information

• Chemical Name: (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one
• CAS No.: 253327-54-7
• Molecular Formula: C₁₅H₂₂INO₂Si
• Molecular Weight: 403.335
• Mol file: 253327-54-7.mol

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

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

There total 1 articles about (3R,4S)-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: 77.0%

[1-(3-Iodo-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine (253327-53-6) + Lithium; (Z)-2-(tert-butyl-dimethyl-silanyloxy)-1-{(1S,2R,4R)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yloxy}-ethenolate → (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-54-7)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃;

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

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:

(3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-iodo-phenyl)-azetidin-2-one (253327-54-7) → C49H53NO14

Guidance literature:

Multi-step reaction with 7 steps

1: 50 percent / Et₃N; DMAP / CH₂Cl₂

2: 40 percent / NaH / tetrahydrofuran / 0 - 35 °C

3: 63 percent / aq. t-BuOK / tetrahydrofuran / -42 - -15 °C

4: 87 percent / DCC; DMAP / toluene / 55 °C

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

6: 76 percent / pyridine*HF

7: 85 percent / H₂ / Pd/C

With dmap; palladium diacetate; silver (II) carbonate; potassium tert-butylate; hydrogen; sodium hydride; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; 1: Acylation / 2: Addition / 3: Hydrolysis / 4: Esterification / 5: Heck macrocyclization / 6: desilylation / 7: Catalytic hydrogenation;

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

upstream raw materials:

[1-(3-Iodo-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine

Downstream raw materials:

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

C₆₁H₇₉NO₁₄Si₂

C₆₁H₈₀INO₁₄Si₂