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

Base Information

Chemical Name:(4R,5S)-ethyl 5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate
CAS No.:1586033-50-2
Molecular Formula:C₃₂H₄₈O₅Si
Molecular Weight:540.816
Hs Code.:

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

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

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

There total 5 articles about (4R,5S)-ethyl 5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolane-4-carboxylate 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: 88.0%

: 1586033-49-9
(2R,3S,4R)-ethyl 4-(tert-butyldiphenylsilyloxy)-2,3-dihydroxyundecanoate

: 77-76-9
2,2-dimethoxy-propane

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

Guidance literature:: With camphorsulphonic acid; In dichloromethane; at 20 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-59-1
C₉H₁₈O₂

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

Guidance literature:: Multi-step reaction with 4 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

With 1H-imidazole; dmap; osmium(VIII) oxide; sodium 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

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

Guidance literature:: Multi-step reaction with 2 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

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