(2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene

Base Information

• Chemical Name: (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene
• CAS No.: 170081-24-0
• Molecular Formula: C₁₉H₃₂O₃Si
• Molecular Weight: 336.547
• Mol file: 170081-24-0.mol

Synonyms:(2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene

Chemical Property of (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene

There total 9 articles about (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene 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: 99.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (2S,3S)-5-(4-methoxyphenyl)-2-methyl-(4E)-penten-1,3-diol (151121-11-8) → (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene (170081-24-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h;

DOI:10.1248/cpb.43.1111

Reference yield:

4-methoxy-trans-cinnamaldehyde (24680-50-0,71277-11-7,1963-36-6) → (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene (170081-24-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 42 percent / Zn / benzene / 1 h / Heating

2: 92 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / diethyl ether / 0.5 h / Ambient temperature

3: 14 percent / Zn(BH₄)2 / diethyl ether / 0 °C

4: 96 percent / LiBH₄ / tetrahydrofuran / 0.5 h / Ambient temperature

6: 99 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; lithium borohydride; zinc(II) tetrahydroborate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.43.1111

Reference yield:

methyl 5-(4-methoxyphenyl)-2-methyl-3-oxopent-4-enoate (126753-78-4) → (2S,3S)-1-tert-butyldimethylsiloxy-3-hydroxy-5-(4-methoxyphenyl)-2-methyl-(4E)-pentene (170081-24-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 2 percent / Zn(BH₄)2 / diethyl ether / 0 °C

2: 96 percent / LiBH₄ / tetrahydrofuran / 0.25 h / Ambient temperature

3: 85 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / diethyl ether / 0.25 h / Ambient temperature

4: Zn(BH₄)2 / diethyl ether / 1 h / 0 °C

6: 99 percent / imidazole / dimethylformamide / 1 h / 0 °C

With 1H-imidazole; lithium borohydride; zinc(II) tetrahydroborate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1248/cpb.43.1111

upstream raw materials:

tert-butyldimethylsilyl chloride

(2S,3S)-5-(4-methoxyphenyl)-2-methyl-(4E)-penten-1,3-diol

4-methoxy-trans-cinnamaldehyde

methyl 5-(4-methoxyphenyl)-2-methyl-3-oxopent-4-enoate

Downstream raw materials:

(2S,3S)-3-methoxy-5-(4-methoxyphenyl)-2-methyl-(4E)-penten-1-ol

(-)-oudemansin X

methyl (E)-(3S,4R)-4-methoxy-6-(4-methoxyphenyl)-3-methylhex-5-enoate

(E)-(3S,4R)-4-Methoxy-6-(4-methoxy-phenyl)-3-methyl-hex-5-enoic acid