[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

Base Information

Chemical Name:[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol
CAS No.:666753-23-7
Molecular Formula:C₂₁H₂₆O₅
Molecular Weight:358.434
Hs Code.:

Synonyms:[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

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Chemical Property of [5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

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Technology Process of [5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

There total 9 articles about [5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol 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: 70.0%

: 110-00-9
furan

: 726203-41-4
(4R,5R)-5-((R)-1-Benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 666753-23-7
[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

Guidance literature:: furan; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

(4R,5R)-5-((R)-1-Benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde; In tetrahydrofuran; at -78 ℃; for 3.5h;

Reference yield:

: 213767-09-0
2,3-O-isopropylidene-L-erythrofuranose

: 666753-23-7
[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

Guidance literature:: Multi-step reaction with 6 steps

1.1: Mg / diethyl ether / 0.5 h / Heating

1.2: diethyl ether / 5 h / -78 - 20 °C

2.1: imidazole / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

3.1: NaH / tetrahydrofuran / 3 h / 0 °C

4.1: 0.174 g / n-Bu₄NF / tetrahydrofuran / 2 h / 20 °C

5.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi / hexane; tetrahydrofuran / 3 h / 0 °C

6.2: 0.86 g / tetrahydrofuran / 3 h / -78 °C

With 1H-imidazole; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydride; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; 5.1: Swern oxidation;
DOI:10.1016/j.tet.2004.04.003

Reference yield:

: 726203-40-3
[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]methanol

: 666753-23-7
[5-(1-benzyloxy-but-3-enyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-furan-2-yl-methanol

Guidance literature:: Multi-step reaction with 2 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 3 h / 0 °C

2.2: 0.86 g / tetrahydrofuran / 3 h / -78 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Swern oxidation;
DOI:10.1016/j.tet.2004.04.003