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

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Chemical Name:(2S,5R,7S)-2-((E)-4-iodo-2-methylpenta-1,4-dien-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane
CAS No.:1404458-60-1
Molecular Formula:C₂₅H₃₅IO₄
Molecular Weight:526.455
Hs Code.:

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

There total 8 articles about (2S,5R,7S)-2-((E)-4-iodo-2-methylpenta-1,4-dien-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: 63.0%

: 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

: 85970-82-7
3-bromo-2-iodo-1-propene

: 1404458-60-1
(2S,5R,7S)-2-((E)-4-iodo-2-methylpenta-1,4-dien-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: (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; With n-butyllithium; isopropylmagnesium bromide; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Inert atmosphere;

With copper(I) cyanide di(lithium chloride); In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

3-bromo-2-iodo-1-propene; In tetrahydrofuran; hexane; at 0 ℃; for 2h; regioselective reaction; Inert atmosphere;
DOI:10.1021/ol302751b

Reference yield:

: 180592-86-3
(2S,3S)-1-(4-methoxybenzyloxy)-2-methylhex-5-en-3-ol

: 1404458-60-1
(2S,5R,7S)-2-((E)-4-iodo-2-methylpenta-1,4-dien-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 8 steps

1.1: titanium(IV) isopropylate; cyclopentylmagnesium chloride / toluene; diethyl ether / 3 h / -78 - -30 °C

1.2: 9 h / -78 - -30 °C / Inert atmosphere

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

3.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; N-chloro-succinimide; tetrabutyl-ammonium chloride / dichloromethane / 19 h / pH 8.6

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

4.2: 24 h / 20 °C / Inert atmosphere

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

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

6.2: 3 h / 20 °C / Inert atmosphere

6.3: 1 h / Inert atmosphere

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

7.2: 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

8.1: n-butyllithium; isopropylmagnesium bromide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

8.2: 0.25 h / -78 °C / Inert atmosphere

8.3: 2 h / 0 °C / Inert atmosphere

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

Reference yield:

: 1404459-08-0
(2S,3S,10S,Z)-1-(4-methoxybenzyloxy)-2-methyl-7-(trimethylsilylmethylene)tridec-11-yne-3,10-diol

: 1404458-60-1
(2S,5R,7S)-2-((E)-4-iodo-2-methylpenta-1,4-dien-1-yl)-7-((S)-1-(4-methoxybenzyloxy)propan-2-yl)-1,6-dioxaspiro[4.5]decane

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 3 h / 20 °C / Inert atmosphere

2.3: 1 h / Inert atmosphere

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

3.2: 0.5 h / 0 °C / Inert atmosphere; Molecular sieve

4.1: n-butyllithium; isopropylmagnesium bromide / tetrahydrofuran; hexane / 2 h / -78 °C / Inert atmosphere

4.2: 0.25 h / -78 °C / Inert atmosphere

4.3: 2 h / 0 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; zirconocene dichloride; ethanol; isopropylmagnesium bromide; diisobutylaluminium hydride; ozone; solvent red 19; In tetrahydrofuran; methanol; hexane; water;
DOI:10.1021/ol302751b