(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

Base Information

Chemical Name:(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane
CAS No.:327165-44-6
Molecular Formula:C₃₀H₅₂O₇Si
Molecular Weight:552.824
Hs Code.:

Synonyms:(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

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Chemical Property of (2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

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Technology Process of (2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

There total 14 articles about (2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane 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: 95.0%

: 108-24-7
acetic anhydride

: 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

: 327165-44-6
(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

Guidance literature:: With pyridine; In dichloromethane; at 23 ℃; for 38h;
DOI:10.1021/ol0069610

Reference yield:

: 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

: 327165-44-6
(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / LiAlH₄ / tetrahydrofuran / 13 h / 20 °C

2: 94 percent / pyridine / CH₂Cl₂

With pyridine; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja048493l

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

: 327165-44-6
(2S,3S,4S,5S)-1-acetoxy-3-hydroxy-5-p-methoxybenzyloxy-2-(methoxymethyleneoxy)-2-methyl-4-(2E-2-methyl-3-trimethylsilylprop-2-enyl)decane

Guidance literature:: Multi-step reaction with 5 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

5.1: 95 percent / pyridine / CH₂Cl₂ / 38 h / 23 °C

With pyridine; 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