(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Base Information

Chemical Name:(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane
CAS No.:1404459-52-4
Molecular Formula:C₂₂H₃₁IO₄
Molecular Weight:486.39
Hs Code.:

Synonyms:(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

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Chemical Property of (2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

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Technology Process of (2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

There total 7 articles about (2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane 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:

: 1404459-11-5
(2S,5S,7S)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-(prop-1-yn-1-yl)-1,6-dioxaspiro[4.5]decane

: 1404459-52-4
(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

: (2S,5R,7S)-2-((Z)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: (2S,5S,7S)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-2-(prop-1-yn-1-yl)-1,6-dioxaspiro[4.5]decane; With zirconocene dichloride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; at 55 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

With iodine; In tetrahydrofuran; hexane; at 0 ℃; for 0.5h; Overall yield = 69 %; Overall yield = 12.7 mg; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/ol302751b

Reference yield:

: 1404459-03-5
(2S,3S,Z)-10-tert-butyldimethylsilyloxy-1-(4-methoxybenzyloxy)-2-methyl-7-(trimethylsilylmethylene)decane-3-ol

: 1404459-52-4
(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

: (2S,5R,7S)-2-((Z)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 6 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 14 h / 0 - 20 °C / Inert atmosphere

2.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride / dichloromethane / 19 h / pH 8.6

3.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / -78 - 20 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride; ethanol / tetrahydrofuran; water / 69 h / 20 °C

5.1: ozone; solvent red 19 / methanol / 0.02 h / -78 °C

5.2: 3 h / 20 °C / Inert atmosphere

5.3: 1 h / Inert atmosphere

6.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / 55 °C / Inert atmosphere; Molecular sieve

6.2: 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; zirconocene dichloride; ethanol; (-)-N-methylephedrine; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; ozone; triethylamine; solvent red 19; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol302751b

Reference yield:

: C₂₃H₄₀O₄Si

: 1404459-52-4
(2S,5R,7S)-2-((E)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

: (2S,5R,7S)-2-((Z)-2-iodoprop-1-en-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride / dichloromethane / 19 h / pH 8.6

2.1: (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / -78 - 20 °C / Inert atmosphere

2.2: 24 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride; ethanol / tetrahydrofuran; water / 69 h / 20 °C

4.1: ozone; solvent red 19 / methanol / 0.02 h / -78 °C

4.2: 3 h / 20 °C / Inert atmosphere

4.3: 1 h / Inert atmosphere

5.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; hexane / 0.5 h / 55 °C / Inert atmosphere; Molecular sieve

5.2: 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

With hydrogenchloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; zirconocene dichloride; ethanol; (-)-N-methylephedrine; tetrabutyl-ammonium chloride; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; ozone; triethylamine; solvent red 19; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol302751b