(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one

Base Information

• Chemical Name: (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one
• CAS No.: 135413-17-1
• Molecular Formula: C₁₈H₃₃NO₄Si
• Molecular Weight: 355.55
• Mol file: 135413-17-1.mol

Synonyms:(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one

Chemical Property of (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one

There total 9 articles about (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-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: 63.0%

(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one (188396-12-5) → (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1S,3S)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one (175891-54-0) + (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one (135413-17-1)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 1h;

DOI:10.1021/ja962006n

Reference yield: 59.0%

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-3-methoxy-2-oxo-cyclohex-3-enyl)-azetidin-2-one (135297-20-0) → (3S,4R)-3-<(R)-1-tert-butyldimethylsilyloxy-ethyl>-4-<(2'S,6'S)-6'-methoxy-1-oxo-cyclohex-2'-yl>-azetidin-2-one (135297-22-2) + (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one (135413-17-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate;

DOI:10.1016/0960-894X(96)00056-X

Reference yield:

2-methoxycyclohexanone (7429-44-9) → (3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((1R,3R)-3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one (135413-17-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH, KH / 1.) THF, reflux, 2.) THF, reflux, 12 h

2: 1.) NaH / 1.) THF, -20 deg C, 45 min, 2.) THF, -20 deg C, 2 h

3: 2,6-lutidine / CH₂Cl₂ / 0.5 h

4: 43 percent / palladium acetate, triphenylphosphine, formic acid / ethyl acetate / 2.5 h / Heating

5: 63 percent / tetrabutylammonium fluoride, acetic acid / tetrahydrofuran / 1 h

With 2,6-dimethylpyridine; formic acid; tetrabutyl ammonium fluoride; palladium diacetate; potassium hydride; sodium hydride; acetic acid; triphenylphosphine; In tetrahydrofuran; dichloromethane; ethyl acetate;

DOI:10.1021/ja962006n

upstream raw materials:

(6-methoxy-cyclohex-1-enyloxy)-trimethyl-silane

(3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-1-trimethylsilyl-2-azetidinone

(3S,4R)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-((R)-3-methoxy-2-oxo-cyclohex-3-enyl)-azetidin-2-one

(3S,4R)-1-(tert-Butyl-dimethyl-silanyl)-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-(3-methoxy-2-oxo-cyclohexyl)-azetidin-2-one