(2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester

Base Information

• Chemical Name: (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester
• CAS No.: 1021491-73-5
• Molecular Formula: C₁₈H₂₈O₄Si
• Molecular Weight: 336.503

Synonyms:(2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester

Chemical Property of (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester

There total 2 articles about (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester 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: 6.0%

(E)-3-phenylpropenal (14371-10-9) + (Z)-2-(tert-Butyldimethylsiloxy)-1-methoxy-1-(trimethylsiloxy)ethene (150811-51-1) → 2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-3-phenylpentanoic acid methyl ester (1035203-28-1) + (2S,3R,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester + (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester (1021491-73-5)

Guidance literature:

With tetrachlorosilane; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -70 ℃; for 0.5h; Title compound not separated from byproducts.;

DOI:10.1021/jo8006539

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + (Z)-2-(tert-Butyldimethylsiloxy)-1-methoxy-1-(trimethylsiloxy)ethene (150811-51-1) → (2S,3R,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester + (2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester (1021491-73-5)

Guidance literature:

With tin(IV) chloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - -70 ℃; for 0.5h; Title compound not separated from byproducts.;

DOI:10.1002/anie.200705499

Reference yield:

(2R,3S,4E)-2-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-hydroxy-5-phenyl-4-pentenoic acid methyl ester (1021491-73-5) → (2R,3S)-2-[[(1,1-dimethylethyl)(dimethyl)silyl]oxy]-3-hydroxy-5-phenylpentanoic acid methyl ester (1021491-70-2)

Guidance literature:

With hydrogen; platinum on activated charcoal; In ethanol; at 20 ℃; for 6h; under 760.051 Torr;

DOI:10.1021/jo8006539

upstream raw materials:

(E)-3-phenylpropenal

(Z)-2-(tert-Butyldimethylsiloxy)-1-methoxy-1-(trimethylsiloxy)ethene

Downstream raw materials:

(2R,3S)-2-[[(1,1-dimethylethyl)(dimethyl)silyl]oxy]-3-hydroxy-5-phenylpentanoic acid methyl ester

(2R,3S,4E)-2,3-dihydroxy-5-phenyl-4-pentenoic acid methyl ester

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