(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Base Information

Chemical Name:(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde
CAS No.:1586033-51-3
Molecular Formula:C₃₀H₄₄O₄Si
Molecular Weight:496.762
Hs Code.:

Synonyms:(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

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Chemical Property of (4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

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Technology Process of (4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

There total 6 articles about (4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-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: 76.0%

: 1586033-50-2
(4R,5S)-ethyl 5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate

: 1586033-51-3
(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2.5h; Inert atmosphere;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-59-1
C₉H₁₈O₂

: 1586033-51-3
(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap; 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

4.1: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-48-8
(R,Z)-ethyl 4-(tert-butyldiphenylsilyloxy)undec-2-enoate

: 1586033-51-3
(4R,5S)-5-(R)-1-((tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

2: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere

3: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

With osmium(VIII) oxide; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; water;
DOI:10.1016/j.tet.2014.02.072