(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

Base Information

Chemical Name:(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane
CAS No.:141859-10-1
Molecular Formula:C₁₈H₂₆O₃
Molecular Weight:290.403
Hs Code.:

Synonyms:(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

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Chemical Property of (4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

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Technology Process of (4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

There total 14 articles about (4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-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: 91.0%

: 141859-09-8
(4R,5R)-(E)-1-benzyloxy-5-hydroxy-4-hydroxymethylhept-2-ene

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

: 141859-10-1
(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: With pyridinium p-toluenesulfonate; In acetone; for 15h; Ambient temperature;
DOI:10.3987/COM-91-S79

Reference yield:

: 131864-03-4
(R)-3-<(tert-butyldimethylsilyl)oxy>-4-(benzyloxy)but-1-yne

: 141859-10-1
(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 14 steps

1: 1.) n-BuLi / 1.) THF, 0 deg C, 1 h, 2.) THF, 0 deg C, 5 h

2: 99 percent / (i-Pr)2NEt / CH₂Cl₂ / 42 h / Ambient temperature

3: 96 percent / H₂ / Lindlar catalyst / hexane / 760 Torr

4: 100 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1.2 h / Ambient temperature

5: 92 percent / KF-Al₂O₃ / tetrahydrofuran / 25 h / Ambient temperature

6: ethylmagnesium bromide / 1.) THF, 0 deg, 1.5 h, 2.) THF, 0 deg C, 30 min

7: 97 percent / n-BuLi / tetrahydrofuran / 0.17 h / -10 °C

8: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / Ambient temperature

9: 84 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

10: 100 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

11: 82 percent / NaHCO₃, N-bromosuccinimide (NBS) / tetrahydrofuran / 1 h

12: 86 percent / H₂ / PtO₂ / hexane / 1.5 h / Ambient temperature

13: 76 percent / Zn, 35percent HCl / methanol / 2.5 h / Heating

14: 91 percent / pyridinium p-toluenesulfonate / acetone / 15 h / Ambient temperature

With hydrogenchloride; potassium fluoride on basic alumina; N-Bromosuccinimide; n-butyllithium; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; zinc; platinum(IV) oxide; Lindlar's catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; acetone;
DOI:10.3987/COM-91-S79

Reference yield:

: 141859-01-0
(R)-(Z)-1-benzyloxy-5-methoxymethoxypent-4-en-2-ol

: 141859-10-1
(4R,5R)-(E)-5-(3-benzyloxyprop-1-enyl)-4-ethyl-2,2-dimethyl-1,3-dioxane

Guidance literature:: Multi-step reaction with 10 steps

1: 92 percent / KF-Al₂O₃ / tetrahydrofuran / 25 h / Ambient temperature

2: ethylmagnesium bromide / 1.) THF, 0 deg, 1.5 h, 2.) THF, 0 deg C, 30 min

3: 97 percent / n-BuLi / tetrahydrofuran / 0.17 h / -10 °C

4: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.08 h / Ambient temperature

5: 84 percent / PPh₃, diisopropyl azodicarboxylate / tetrahydrofuran / 0.17 h / 0 °C

6: 100 percent / K₂CO₃ / methanol / 2 h / Ambient temperature

7: 82 percent / NaHCO₃, N-bromosuccinimide (NBS) / tetrahydrofuran / 1 h

8: 86 percent / H₂ / PtO₂ / hexane / 1.5 h / Ambient temperature

9: 76 percent / Zn, 35percent HCl / methanol / 2.5 h / Heating

10: 91 percent / pyridinium p-toluenesulfonate / acetone / 15 h / Ambient temperature

With hydrogenchloride; potassium fluoride on basic alumina; N-Bromosuccinimide; n-butyllithium; di-isopropyl azodicarboxylate; ethylmagnesium bromide; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; potassium carbonate; triphenylphosphine; zinc; platinum(IV) oxide; In tetrahydrofuran; methanol; hexane; acetone;
DOI:10.3987/COM-91-S79