(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

Base Information

Chemical Name:(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol
CAS No.:327165-60-6
Molecular Formula:C₂₈H₅₀O₆Si
Molecular Weight:510.787
Hs Code.:

Synonyms:(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

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Chemical Property of (2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

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Technology Process of (2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

There total 13 articles about (2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-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: 93.0%

: 2',6'-di-t-butyl-4'-methylphenyl-(4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3-trimethylsilylprop-2-enyl)decanoate

: 327165-60-6
(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

: (2R,3R,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 13h;
DOI:10.1021/ja048493l

Reference yield: 92.0%

: 327165-43-5
2',6'-di-tert-butyl-4'-methylphenyl (2R,3S,4R,5S)-3-hydroxy-5-(p-methoxybenzyloxy)-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)-decanoate

: 327165-60-6
(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 23 ℃; for 22h;
DOI:10.1021/ol0069610

Reference yield:

: 327165-57-1
{(E)-3-[(4S,5S)-2-(4-Methoxy-phenyl)-4-pentyl-[1,3]dioxan-5-yl]-2-methyl-propenyl}-trimethyl-silane

: 327165-60-6
(2S,3S,4R,5S)-3-hydroxy-5-p-methoxybenzyloxy-2-methoxymethyleneoxy-2-methyl-4-(E-2'-methyl-3'-trimethylsilylprop-2'-enyl)decan-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 91 percent / DIBAL-H / toluene; hexane / 32 h / 23 °C

2.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.5 h / -78 - 0 °C

3.1: LDA / tetrahydrofuran; various solvent(s) / 0.67 h / -78 °C

3.2: tetrahydrofuran; various solvent(s) / 1 h / -78 °C

4.1: 92 percent / LiAlH₄ / tetrahydrofuran / 22 h / 23 °C

With lithium aluminium tetrahydride; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; toluene; 2.1: Swern oxidation;
DOI:10.1021/ol0069610