Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

Base Information

Chemical Name:Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate
CAS No.:223907-23-1
Molecular Formula:C₂₆H₄₀O₄Si
Molecular Weight:444.687
Hs Code.:

Synonyms:Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

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Chemical Property of Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

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Technology Process of Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

There total 5 articles about Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate 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: 54.0%

: 13170-43-9
(trimethylsilyl)methylmagnesium chloride

: 223907-22-0
Methyl (2Z,6E)-3[(diethoxyphosphoryl)oxy]-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]nona-2,6-dienoate

: 223907-23-1
Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

Guidance literature:: With bis(acetylacetonate)nickel(II); In diethyl ether; at 0 ℃; for 0.166667h;
DOI:10.1039/a906589j

Reference yield:

: 908094-04-2
phenyldiazomethane

: Methyl (2Z,6E)-9-[(2S/R,3S/R)-3-(hydroxymethyl)-3-methyloxiran-2-yl]-7-methyl-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

: (2Z,6E)-12-Benzyloxy-7,11-dimethyl-10-oxo-3-trimethylsilanylmethyl-dodeca-2,6-dienoic acid methyl ester

: 223907-23-1
Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

: Methyl (2Z,6E)-7-methyl-9-[(2R,3R)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

Guidance literature:: With tetrafluoroboric acid; In dichloromethane; at -40 ℃; Title compound not separated from byproducts;
DOI:10.1039/a906589j

Reference yield:

: 116179-52-3
(-)-6,7-epoxy-8-(benzyloxy)geranyl alcohol

: 223907-23-1
Methyl (2Z,6E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-[(trimethylsilyl)methyl]nona-2,6-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NEt₃; MeSO₂Cl / tetrahydrofuran / 1 h / -78 °C

1.2: 79 percent / LiBr / tetrahydrofuran; acetone / 0.67 h / -78 °C

2.1: NaH; n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 78 percent / tetrahydrofuran; hexane / 17 h / 20 °C

3.1: NaH / diethyl ether / 0.33 h / 0 °C

3.2: 93 percent / diethyl ether / 2.5 h / 20 °C

4.1: 54 percent / nickel(II) acetylacetonate / diethyl ether / 0.17 h / 0 °C

With bis(acetylacetonate)nickel(II); n-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; diethyl ether; hexane; 1.1: Mesylation / 1.2: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Metallation / 3.2: Esterification / 4.1: Alkylation;
DOI:10.1039/a906589j