(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

Base Information

Chemical Name:(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol
CAS No.:1422039-48-2
Molecular Formula:C₂₆H₄₀O₄
Molecular Weight:416.601
Hs Code.:

Synonyms:(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

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Chemical Property of (R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

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Technology Process of (R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

There total 7 articles about (R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol 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: 78.0%

: 628-71-7
1-Heptyne

: 1422039-46-0
(4R,5S)-4-(5-(benzyloxy)pentyl)-2,2-dimethyl-5-((S)-oxiran-2-yl)-1,3-dioxolane

: 1422039-48-2
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 0.75h;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

: 1422039-44-8
(R)-2-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-hydroxyethyl benzoate

: 1422039-48-2
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice

2: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 4 h / 20 °C

3: n-butyllithium; boron trifluoride diethyl etherate / tetrahydrofuran / 0.75 h / -78 °C

With n-butyllithium; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1016/j.tet.2012.12.045

Reference yield:

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

: 1422039-48-2
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)non-3-yn-1-ol

Guidance literature:: Multi-step reaction with 8 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 / 0 °C

5.2: 8 h / 0 - 20 °C

6.1: triethylamine / dichloromethane / 4 h / 20 °C / Cooling with ice

7.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 4 h / 20 °C

8.1: n-butyllithium; boron trifluoride diethyl etherate / tetrahydrofuran / 0.75 h / -78 °C

With dmap; sodium periodate; n-butyllithium; lithium hydroxide monohydrate; boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; di(n-butyl)tin oxide; 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