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

Base Information

• Chemical Name: (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one
• CAS No.: 253327-67-2
• Molecular Formula: C₂₂H₃₉NO₃Si₂
• Molecular Weight: 421.728

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

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

Chemical Property:

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Technology Process of (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one

There total 12 articles about (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-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:

3-(hydroxymethyl)benzaldehyde (52010-98-7) → (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one (253327-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 82 percent / Et₃N / CH₂Cl₂

2: 100 percent / tetrahydrofuran

3: tetrahydrofuran / -78 - 20 °C

With triethylamine; In tetrahydrofuran; dichloromethane; 1: silylation / 2: amidosilylation / 3: asymmetric cyclocondensation;

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

Reference yield:

C16H25NO3Si + tert-butyldimethylsilyl chloride (18162-48-6) → (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one (253327-67-2)

Guidance literature:

With pyridine; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1021/acs.jnatprod.7b00857

Reference yield:

[1-(3-Triethylsilanyloxymethyl-phenyl)-meth-(E)-ylidene]-trimethylsilanyl-amine (253327-66-1) + 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 → (3S,4R)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one + (3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-4-(3-triethylsilanyloxymethyl-phenyl)-azetidin-2-one (253327-67-2)

Guidance literature:

In tetrahydrofuran; at -78 - 20 ℃; Title compound not separated from byproducts;

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

upstream raw materials:

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

3-(hydroxymethyl)benzaldehyde

3-triethylsilanyloxymethyl-benzaldehyde

Isophthalaldehyde

Downstream raw materials:

C₇₄H₉₁NO₁₇Si₂

C₆₀H₇₉NO₁₇Si₂

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