(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol

Base Information

Chemical Name:(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol
CAS No.:1112844-72-0
Molecular Formula:C₄₂H₇₄O₅Si
Molecular Weight:687.132
Hs Code.:

Synonyms:(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-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)-19-(tert-butyldimethylsilyloxy)nonadec-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)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol

There total 11 articles about (R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-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: 82.0%

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

: 1112844-55-9
tert-butyl(heptadec-16-ynyloxy)dimethylsilane

: 1112844-72-0
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol

Guidance literature:: With n-butyllithium; boron trifluoride diethyl etherate; In tetrahydrofuran; at -78 ℃; for 1h;
DOI:10.1016/j.tetlet.2008.10.137

Reference yield:

: 69502-96-1
2-(heptadec-2-ynyloxy)tetrahydro-2H-pyran

: 1112844-72-0
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: toluene-4-sulfonic acid / methanol / 0.5 h / 20 °C

2.1: potassium tert-butylate; lithium / 1 h / 20 °C

3.1: dmap; triethylamine / dichloromethane / 0.25 h / 0 °C

3.2: 1 h / 0 °C

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

With dmap; n-butyllithium; boron trifluoride diethyl etherate; potassium tert-butylate; lithium; toluene-4-sulfonic acid; 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

: 1112844-72-0
(R)-1-((4R,5R)-5-(5-(benzyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-19-(tert-butyldimethylsilyloxy)nonadec-3-yn-1-ol

Guidance literature:: Multi-step reaction with 7 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

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

With dmap; sodium periodate; n-butyllithium; boron trifluoride diethyl etherate; 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