(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

Base Information

Chemical Name:(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione
CAS No.:1373358-11-2
Molecular Formula:C₂₅H₂₅NO₅S
Molecular Weight:451.543
Hs Code.:

Synonyms:(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

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Chemical Property of (R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

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Technology Process of (R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

There total 8 articles about (R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione 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: 55.0%

: 1373358-10-1
(R)-1,6-dioxo-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-9-carbaldehyde

: 1826-67-1
vinyl magnesium bromide

: 1373358-11-2
(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

Guidance literature:: (R)-1,6-dioxo-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-9-carbaldehyde; vinyl magnesium bromide; In tetrahydrofuran; at -40 - -10 ℃; for 2.5h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran;
DOI:10.1002/anie.201107716

Reference yield:

: 1207681-12-6
methyl 2-((4-methoxyphenyl)(tosylimino)methyl)acrylate

: 1373358-11-2
(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; acetic acid / water; toluene / -13 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 7 h / 36 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

3.2: 2 h / 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2.5 h / -40 - -10 °C / Inert atmosphere

With 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Diels-Alder reaction;
DOI:10.1002/anie.201107716

Reference yield:

: 1373357-77-7
C₆H₇O₂^(1-)*K⁽¹⁺⁾

: 1373358-11-2
(R)-9-((S)-1-hydroxyallyl)-8-phenyl-7-tosyl-7-azaspiro[4.5]dec-8-ene-1,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; acetic acid / water; toluene / -13 °C / Inert atmosphere

2.1: pyridinium chlorochromate / dichloromethane / 7 h / 36 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C

3.2: 2 h / 20 °C

4.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 2 h / 20 °C / Inert atmosphere

5.1: tetrahydrofuran / 2.5 h / -40 - -10 °C / Inert atmosphere

With 1-((1S,2S)-2-aminocyclohexyl)-3-(((1R,4aS,10ar)-7-isopropyl-1,4a-dimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthren-1-yl)methyl)thiourea; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.1: Diels-Alder reaction;
DOI:10.1002/anie.201107716