(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

Base Information

Chemical Name:(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane
CAS No.:1395342-40-1
Molecular Formula:C₂₀H₂₇BrO₂
Molecular Weight:379.337
Hs Code.:

Synonyms:(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

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Chemical Property of (2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

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Technology Process of (2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

There total 13 articles about (2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane 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: 81.0%

: 1395342-38-7
(2R,3R,9R,10S,E)-3-allyl-2,10-bis((triethylsilyl)oxy)-9-methyl-10-(4-bromophenyl)-decane-6-one

: 1395342-40-1
(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

: 1395342-56-9
(2R,3S,6R,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

Guidance literature:: With hydrogen fluoride; In tetrahydrofuran; water; at 20 ℃; optical yield given as %de; stereoselective reaction; Inert atmosphere;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-30-9
(2S,3S)-3-(4-bromophenyl)-2-methyl-3-((triethylsilyl)oxy)propanal

: 1395342-40-1
(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

: 1395342-56-9
(2R,3S,6R,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrahydrofuran / 20 °C / Inert atmosphere; Reflux

2.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / 5 h / Inert atmosphere; Reflux

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

4.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

4.2: 20 °C / Inert atmosphere

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -50 °C / Inert atmosphere

5.2: 1 h / -50 °C / Inert atmosphere

6.1: hydrogen fluoride / tetrahydrofuran; water / 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; hydrogen fluoride; methyllithium; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid hydrazide; barium(II) hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; 1.1: Wittig reaction / 3.2: Claisen condensation / 4.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1290670

Reference yield:

: 1395342-46-7
(4R,5S,E)-ethyl-5-(4-bromophenyl)-4-methyl-5-((triethylsilyl)oxy)pent-2-enoate

: 1395342-40-1
(2R,3S,6S,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

: 1395342-56-9
(2R,3S,6R,8S,9R)-3-allyl-8-(4-bromophenyl)-2,9-dimethyl-1,7-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / 5 h / Inert atmosphere; Reflux

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: barium(II) hydroxide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

3.2: 20 °C / Inert atmosphere

4.1: N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; methyllithium; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / -50 °C / Inert atmosphere

4.2: 1 h / -50 °C / Inert atmosphere

5.1: hydrogen fluoride / tetrahydrofuran; water / 20 °C / Inert atmosphere

With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; n-butyllithium; hydrogen fluoride; methyllithium; sodium acetate; diisobutylaluminium hydride; toluene-4-sulfonic acid hydrazide; barium(II) hydroxide; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; water; 2.2: Claisen condensation / 3.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1055/s-0031-1290670