Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

Base Information

Chemical Name:Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate
CAS No.:223907-20-8
Molecular Formula:C₂₂H₃₀O₅
Molecular Weight:374.477
Hs Code.:

Synonyms:Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

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Chemical Property of Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

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Technology Process of Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

There total 2 articles about Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate 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: 78.0%

: 105-45-3
acetoacetic acid methyl ester

: 223907-19-5
(2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane

: 223907-20-8
Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

Guidance literature:: acetoacetic acid methyl ester; With n-butyllithium; sodium hydride; In tetrahydrofuran; hexane; at 0 ℃; for 0.333333h;

(2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane; In tetrahydrofuran; hexane; at 20 ℃; for 17h;
DOI:10.1039/a906589j

Reference yield:

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

: 223907-20-8
Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

Guidance literature:: Multi-step reaction with 2 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

With n-butyllithium; sodium hydride; methanesulfonyl chloride; triethylamine; In tetrahydrofuran; hexane; 1.1: Mesylation / 1.2: Substitution / 2.1: Metallation / 2.2: Alkylation;
DOI:10.1039/a906589j

Reference yield: 93.0%

: 814-49-3
diethyl chlorophosphate

: 223907-20-8
Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate

: 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

Guidance literature:: Methyl (E)-7-methyl-9-[(2S,3S)-3-methyl-3-(benzyloxymethyl)oxiran-2-yl]-3-oxonon-6-enoate; With sodium hydride; In diethyl ether; at 0 ℃; for 0.333333h;

diethyl chlorophosphate; In diethyl ether; at 20 ℃; for 2.5h;
DOI:10.1039/a906589j