(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde
CAS No.:366011-46-3
Molecular Formula:C₂₀H₁₉IO₄
Molecular Weight:450.273
Hs Code.:

Synonyms:(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Chemical Property of (4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

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Technology Process of (4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

There total 7 articles about (4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 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: 91.0%

: 366011-45-2
[(4S,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-methanol

: 366011-46-3
(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 21 ℃; for 1h;
DOI:10.1560/7J4F-D8BG-3FQR-E3TD

Reference yield:

: 100-39-0
benzyl bromide

: 366011-46-3
(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1.1: 88 percent / NaH / tetrahydrofuran / 17 h / 21 °C

2.1: 93 percent / TBAF / tetrahydrofuran / 4 h / -78 - 0 °C

3.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

3.2: 93 percent / I₂ / tetrahydrofuran; hexane / 7.5 h / -78 - 0 °C

4.1: 91 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

With tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 4.1: Dess-Martin oxidation;
DOI:10.1560/7J4F-D8BG-3FQR-E3TD

Reference yield:

: 108817-97-6
(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

: 366011-46-3
(4R,5S)-5-((Z)-(R)-1-Benzyloxy-7-iodo-hept-4-ene-2,6-diynyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran / 0.33 h

1.2: 86 percent / tetrahydrofuran / 0.5 h / -78 °C

2.1: 88 percent / NaH / tetrahydrofuran / 17 h / 21 °C

3.1: 93 percent / TBAF / tetrahydrofuran / 4 h / -78 - 0 °C

4.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 93 percent / I₂ / tetrahydrofuran; hexane / 7.5 h / -78 - 0 °C

5.1: 91 percent / NaHCO₃; Dess-Martin periodinane / CH₂Cl₂ / 1 h / 21 °C

With n-butyllithium; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane; 5.1: Dess-Martin oxidation;
DOI:10.1560/7J4F-D8BG-3FQR-E3TD