(2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol

Base Information

• Chemical Name: (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol
• CAS No.: 1446121-44-3
• Molecular Formula: C₁₇H₃₀O₃Si
• Molecular Weight: 310.509

Synonyms:(2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol

Chemical Property of (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol

There total 3 articles about (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol 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: 64.0%

(S)-4-benzyl-3-((2R,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropanoyl)oxazolidin-2-one (1446121-37-4) → (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol (1446121-44-3)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; ethanol; at 0 ℃; for 1h;

DOI:10.1021/ol401458d

Reference yield:

4-methoxy-benzaldehyde (123-11-5) → (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol (1446121-44-3)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; magnesium chloride; chloro-trimethyl-silane / ethyl acetate / 36 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

3: lithium borohydride / tetrahydrofuran; ethanol / 1 h / 0 °C

With lithium borohydride; chloro-trimethyl-silane; triethylamine; N-ethyl-N,N-diisopropylamine; magnesium chloride; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate;

DOI:10.1021/ol401458d

Reference yield:

(4S)-3-[(3S,2R)-3-hydroxy-3-(4-methoxyphenyl)-2-methylpropanoyl]-4-benzyl-1,3-oxazolidin-2-one → (2S,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropan-1-ol (1446121-44-3)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / -78 °C / Inert atmosphere

2: lithium borohydride / tetrahydrofuran; ethanol / 1 h / 0 °C

With lithium borohydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ol401458d

upstream raw materials:

(S)-4-benzyl-3-((2R,3S)-3-(tert-butyldimethylsilyloxy)-3-(4-methoxyphenyl)-2-methylpropanoyl)oxazolidin-2-one

4-methoxy-benzaldehyde

Downstream raw materials:

tert-butyl((1S,2S)-1-(4-methoxyphenyl)-2-methylbut-3-enyloxy)dimethylsilane

(R)-((1S,2S)-1-(4-methoxyphenyl)-2-methylbut-3-enyl) 3-(tert-butyl dimethylsilyloxy)-5-((4R,5S)-2,2,4-trimethyl-5-vinyl-1,3-dioxolan-4-yl)pentanoate

(3R,6R,7S)-((1S,2S)-1-(4-methoxyphenyl)-2-methylbut-3-enyl) 3,6,7-tri-hydroxy-6-methylnon-8-enoate

(4R,7R,8S,11RS₁₂S,E)-4,7,8-trihydroxy-12-(4-methoxyphenyl)-7,11-dimethyloxacyclododec-9-en-2-one

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