(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane
CAS No.:1351684-98-4
Molecular Formula:C₁₈H₂₆O₃
Molecular Weight:290.403
Hs Code.:

Synonyms:(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

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Chemical Property of (4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

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Technology Process of (4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

There total 7 articles about (4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane 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: 95.0%

: 1351684-96-2
(2R,4S,Z)-1-(benzyloxy)oct-5-ene-2,4-diol

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

: 1351684-98-4
(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.069

Reference yield:

: 1351684-94-0
(2R,4S)-1-(benzyloxy)-2-((tert-butyldimethylsilyl)oxy)oct-5-yn-4-ol

: 1351684-98-4
(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine; 1-hexene; hydrogen / ethyl acetate / 8 h

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; 1-hexene; tetrabutyl ammonium fluoride; hydrogen; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2011.09.069

Reference yield:

: 1351684-80-4
(R)-benzyl 4-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-butanoate

: 1351684-98-4
(4R,6S)-4-((benzyloxy)methyl)-6-((Z)-but-1-en-1-yl)-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 5 steps

1.1: diisobutylaluminium hydride / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.2: -78 - 20 °C / Inert atmosphere

2.3: 20 °C / Inert atmosphere

3.1: pyridine; 1-hexene; hydrogen / ethyl acetate / 8 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; n-butyllithium; 1-hexene; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2011.09.069