tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

Base Information

Chemical Name:tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate
CAS No.:1315613-96-7
Molecular Formula:C₃₁H₅₀BrNO₇Si
Molecular Weight:656.73
Hs Code.:

tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

Synonyms:tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

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Chemical Property of tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

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Technology Process of tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

There total 9 articles about tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate 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: 76.0%

: N-[2-[(5S,6R)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-hydroxy-1-cyclohexen-1-yl]ethyl]-N-methyl-carbamic acid 1,1-dimethylethyl ester

: 1315613-93-4
2-bromo-3-(1,3-dioxolan-2-ylmethyl)-6-methoxyphenol

: 1315613-96-7
tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

Guidance literature:: With tributylphosphine; di-isopropyl azodicarboxylate; In tetrahydrofuran; at 4 - 25 ℃; for 12h; Inert atmosphere;
DOI:10.1139/v11-071

Reference yield:

: 621-59-0
isovanillin

: 1315613-96-7
tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1.1: N-Bromosuccinimide / chloroform / Inert atmosphere; Reflux

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: 3.58 h / 0 °C / Inert atmosphere; Reflux

4.1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / Inert atmosphere; Reflux

5.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 4 - 25 °C / Inert atmosphere

With N-Bromosuccinimide; tributylphosphine; di-isopropyl azodicarboxylate; tert.-butyl lithium; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; chloroform; 3.1: Wittig reaction / 3.2: Wittig reaction / 5.1: Mitsunobu reaction;
DOI:10.1139/v11-071

Reference yield:

: 1315613-94-5
C₁₁H₁₇BrO₂

: 1315613-96-7
tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

Guidance literature:: Multi-step reaction with 5 steps

1: potassium carbonate / tetrahydrofuran / 18.25 h / -40 - 25 °C / Inert atmosphere

2: hydrogenchloride / ethanol; water / 4 h / Inert atmosphere

3: ethanol; water / 4 h / Inert atmosphere

4: 1H-imidazole / dichloromethane / -78 - 25 °C / Inert atmosphere

5: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 4 - 25 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; tributylphosphine; di-isopropyl azodicarboxylate; potassium carbonate; In tetrahydrofuran; ethanol; dichloromethane; water; 5: Mitsunobu reaction;
DOI:10.1139/v11-071