(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

Base Information

Chemical Name:(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane
CAS No.:1112844-52-6
Molecular Formula:C₁₉H₂₈O₄
Molecular Weight:320.429
Hs Code.:

Synonyms:(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

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Chemical Property of (4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

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Technology Process of (4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

There total 6 articles about (4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane 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: 92.0%

: 1112844-65-1
(R)-2-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl 4-methyl-benzenesulfonate

: 1112844-52-6
(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

Guidance literature:: With potassium carbonate; In methanol; for 1h;
DOI:10.1016/j.tetlet.2008.10.137

Reference yield:

: 38145-93-6
1,2:3,4-di-O-isopropylidene-D-mannitol

: 1112844-52-6
(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: sodium periodate / dichloromethane; water / 4 h / 0 - 20 °C

2.1: potassium tert-butylate / tetrahydrofuran / 0 °C

2.2: 0.5 h / 0 °C

3.1: hydrogen / ethanol / 0.5 h / 1034.32 Torr

4.1: toluene-4-sulfonic acid / methanol / 20 h / 0 °C

5.1: di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice

5.2: 4 h / 0 - 20 °C

6.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

With dmap; sodium periodate; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; 2.1: |Wittig Olefination / 2.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 13039-93-5
2,2:4,5-di-O-isopropylidene-D-arabinose

: 1112844-52-6
(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolane

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium tert-butylate / tetrahydrofuran / 0 °C

1.2: 0.5 h / 0 °C

2.1: hydrogen / ethanol / 0.5 h / 1034.32 Torr

3.1: toluene-4-sulfonic acid / methanol / 20 h / 0 °C

4.1: di(n-butyl)tin oxide; dmap; triethylamine / dichloromethane / 0.5 h / 20 °C / Cooling with ice

4.2: 4 h / 0 - 20 °C

5.1: potassium carbonate / methanol / 1 h / 0 °C / Inert atmosphere

With dmap; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; potassium carbonate; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1.1: |Wittig Olefination / 1.2: |Wittig Olefination;
DOI:10.1016/j.tet.2012.12.045