(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

Base Information

Chemical Name:(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol
CAS No.:646520-56-1
Molecular Formula:C₂₄H₄₀O₆Si
Molecular Weight:452.663
Hs Code.:

Synonyms:(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

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Chemical Property of (5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

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Technology Process of (5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

There total 6 articles about (5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-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: 94.0%

: 18295-60-8
allenylmagnesium bromide

: 646520-55-0
{2-[(1S,3S)-3-Methoxy-1-(4-methoxy-benzyloxymethyl)-3-(S)-oxiranyl-propoxymethoxy]-ethyl}-trimethyl-silane

: 646520-56-1
(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

Guidance literature:: In diethyl ether; at -78 ℃; for 1.08333h;
DOI:10.1021/ja0304953

Reference yield:

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 646520-56-1
(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / diisopropylethylamine; tetra-n-butylammonium chloride / CH₂Cl₂ / 7 h / 40 °C

2.1: 81 percent / lithium triethylborohydride / tetrahydrofuran / 3 h / 0 °C

3.1: NaH / dimethylformamide / 1.5 h / 25 °C

3.2: 83 percent / tetra-n-butylammnonium iodide / dimethylformamide / 24 h / 25 °C

4.1: 88 percent / aq. acetic acid / 15 h / 25 °C

5.1: trimethylorthoacetate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.75 h / 25 °C

5.2: acetyl chloride / CH₂Cl₂ / 5 h / 25 °C

5.3: 88 percent / K₂CO₃ / methanol / 12 h / 25 °C

6.1: 94 percent / diethyl ether / 1.08 h / -78 °C

With Trimethyl orthoacetate; tetrabutyl-ammonium chloride; pyridinium p-toluenesulfonate; sodium hydride; lithium triethylborohydride; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0304953

Reference yield:

: 646520-52-7
(2S,4S)-4-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-4-methoxy-2-(2-trimethylsilanyl-ethoxymethoxy)-butan-1-ol

: 646520-56-1
(5S,6S,8S)-6-Methoxy-9-(4-methoxy-benzyloxy)-8-(2-trimethylsilanyl-ethoxymethoxy)-non-1-yn-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / dimethylformamide / 1.5 h / 25 °C

1.2: 83 percent / tetra-n-butylammnonium iodide / dimethylformamide / 24 h / 25 °C

2.1: 88 percent / aq. acetic acid / 15 h / 25 °C

3.1: trimethylorthoacetate; pyridinium p-toluenesulfonate / CH₂Cl₂ / 0.75 h / 25 °C

3.2: acetyl chloride / CH₂Cl₂ / 5 h / 25 °C

3.3: 88 percent / K₂CO₃ / methanol / 12 h / 25 °C

4.1: 94 percent / diethyl ether / 1.08 h / -78 °C

With Trimethyl orthoacetate; pyridinium p-toluenesulfonate; sodium hydride; acetic acid; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0304953