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

Base Information

Chemical Name:(2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane
CAS No.:223907-19-5
Molecular Formula:C₁₇H₂₃BrO₂
Molecular Weight:339.272
Hs Code.:

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

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Chemical Property of (2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane

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Technology Process of (2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane

There total 1 articles about (2S,3S)-3-[(E)-5-bromo-3-methylpent-3-enyl]-2-methyl-2-(benzyloxymethyl)oxirane 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: 79.0%

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

: 116179-53-4
(+)-6,7-epoxy-8-(benzyloxy)geranyl chloride

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

Guidance literature:: (-)-6,7-epoxy-8-(benzyloxy)geranyl alcohol; With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at -78 ℃; for 1h;

With lithium bromide; In tetrahydrofuran; acetone; at -78 ℃; for 0.666667h;
DOI:10.1039/a906589j

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:

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

: (4aR,5R,6S,8aS)-6-Benzyloxy-5-benzyloxymethyl-2,5,8a-trimethyl-1,4,4a,5,6,7,8,8a-octahydro-naphthalene-1-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: 78 percent / tetrahydrofuran; hexane / 17 h / 20 °C

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

2.2: 93 percent / diethyl ether / 2.5 h / 20 °C

3.1: 54 percent / nickel(II) acetylacetonate / diethyl ether / 0.17 h / 0 °C

4.1: 54 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.17 h / 20 °C

5.1: NaH / tetrahydrofuran / 1 h / Heating

5.2: 42 percent / tetrahydrofuran / Heating

6.1: RhCl₃ / ethanol / Heating

With bis(acetylacetonate)nickel(II); n-butyllithium; boron trifluoride diethyl etherate; sodium hydride; rhodium(III) chloride; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 1.1: Metallation / 1.2: Alkylation / 2.1: Metallation / 2.2: Esterification / 3.1: Alkylation / 4.1: Cyclization / 5.1: Metallation / 5.2: Alkylation / 6.1: Isomerization;
DOI:10.1039/a906589j