(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole
• CAS No.: 1312551-56-6
• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.439

Synonyms:(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole

Chemical Property of (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole

Chemical Property:

Purity/Quality:

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Technology Process of (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole

There total 5 articles about (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole 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: 50.0%

n-butyl(triphenyl)phosphonium bromide (1779-51-7) + 6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-carbaldehyde (138513-24-3) → (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole (1312551-56-6)

Guidance literature:

n-butyl(triphenyl)phosphonium bromide; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 6h; Inert atmosphere;

6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-carbaldehyde; In tetrahydrofuran; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1039/c1ob00019e

Reference yield:

6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5S,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl-methyl tert-butyldiphenylsilyl ether (1312551-39-5) → (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole (1312551-56-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 10 - 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With potassium tert-butylate; tetrabutyl ammonium fluoride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1039/c1ob00019e

Reference yield:

(3aR,5S,6S,6aR)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-ol (103763-14-0) → (3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-((E)-pent-1-enyl)furo[3,2-d][1,3]dioxole (1312551-56-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 10 - 20 °C / Inert atmosphere

4.1: potassium tert-butylate / tetrahydrofuran / 6 h / 0 °C / Inert atmosphere

4.2: 0 - 20 °C / Inert atmosphere

With potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dimethyl sulfoxide;

DOI:10.1039/c1ob00019e

upstream raw materials:

6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5S,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl-methyl tert-butyldiphenylsilyl ether

6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5S,6S,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-yl-methanol

n-butyl(triphenyl)phosphonium bromide

6-(4-methoxybenzyloxy)-2,2-dimethyl-(3aR,5R,6R,6aR)-perhydrofuro[2,3-d][1,3]dioxol-5-carbaldehyde

Downstream raw materials:

(3aR,5S,6S,6aR)-6-(4-methoxybenzyloxy)-tetrahydro-2,2-dimethyl-5-n-pentylfuro[3,2-d][1,3]dioxole

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