tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

Base Information

Chemical Name:tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate
CAS No.:1312102-33-2
Molecular Formula:C₁₉H₂₁NO₈
Molecular Weight:391.378
Hs Code.:

Synonyms:tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

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Chemical Property of tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

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Technology Process of tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

There total 5 articles about tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate 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: 60.0%

: 1092850-40-2
tert-butyl 2-(3,6-dioxo-3,6-dihydro-2H-pyran-2-yl)acetate

: 22568-49-6
(E)-1-(4-hydroxyphenyl)-2-nitroethene

: tert-butyl 2-{(1R,4R,7R,8R)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

: 1312102-33-2
tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

Guidance literature:: (E)-1-(4-hydroxyphenyl)-2-nitroethene; With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; formic acid; In isopropyl alcohol; at 20 ℃; for 0.5h;

tert-butyl 2-(3,6-dioxo-3,6-dihydro-2H-pyran-2-yl)acetate; In isopropyl alcohol; at 20 ℃; for 26h; optical yield given as %ee; enantioselective reaction;
DOI:10.1002/adsc.201000927

Reference yield:

: 98-01-1
furfural

: tert-butyl 2-{(1R,4R,7R,8R)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

: 1312102-33-2
tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium diisopropyl amide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

1.2: 1.5 h / -78 °C / Inert atmosphere

2.1: N-Bromosuccinimide; sodium acetate; sodium hydrogencarbonate / tetrahydrofuran; water / 0.17 h / 0 °C

3.1: Jones reagent / acetone / 0.5 h / 0 °C

4.1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; formic acid / isopropyl alcohol / 0.5 h / 20 °C

4.2: 26 h / 20 °C

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; N-Bromosuccinimide; Jones reagent; formic acid; sodium acetate; sodium hydrogencarbonate; lithium diisopropyl amide; In tetrahydrofuran; water; isopropyl alcohol; acetone; 3.1: Jones oxidation / 4.1: Diels-Alder reaction / 4.2: Diels-Alder reaction;
DOI:10.1002/adsc.201000927

Reference yield:

: C₁₁H₂₀O₅

: tert-butyl 2-{(1R,4R,7R,8R)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

: 1312102-33-2
tert-butyl 2-{(1R,4R,7S,8S)-7-(4-hydroxyphenyl)-8-nitro-3,6-dioxo-2-oxabicyclo[2.2.2]octan-1-yl}acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: Jones reagent / acetone / 0.5 h / 0 °C

2.1: 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; formic acid / isopropyl alcohol / 0.5 h / 20 °C

2.2: 26 h / 20 °C

With 1-(3,5-bis(trifluoromethyl)phenyl)-3-((S)-(6-methoxyquinolin-4-yl)((2S,4S,8R)-8-vinylquinuclidin-2-yl)methyl)thiourea; Jones reagent; formic acid; In isopropyl alcohol; acetone; 1.1: Jones oxidation / 2.1: Diels-Alder reaction / 2.2: Diels-Alder reaction;
DOI:10.1002/adsc.201000927