(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Base Information

Chemical Name:(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran
CAS No.:389860-58-6
Molecular Formula:C₂₁H₂₈O₅
Molecular Weight:360.45
Hs Code.:

Synonyms:(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

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Chemical Property of (2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

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Technology Process of (2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

There total 5 articles about (2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran 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: 85.4%

: 676-58-4
methylmagnesium chloride

: 389860-57-5
(2R,5S,6R,1'E)-6-(3'-acetoxyprop-1'-enyl)-5,6-dihidro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

: 389860-58-6
(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Guidance literature:: With dilithium tetrachlorocuprate; In tetrahydrofuran; at -8 ℃; for 1h;
DOI:10.1039/b104341m

Reference yield:

: (2S,3S,6R)-6-(4-Methoxy-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-2-carbaldehyde

: 389860-58-6
(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 0 °C

1.2: 4.50 g / tetrahydrofuran / -20 - 0 °C

2.1: 84 percent / DIBAL-H / diethyl ether / 1 h / -78 °C

3.1: 100 percent / pyridine / 1 h / 20 °C

4.1: 85.4 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / -8 °C

With pyridine; dilithium tetrachlorocuprate; sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether;
DOI:10.1039/b104341m

Reference yield:

: [(2R,3S,6R)-6-(4-Methoxy-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-3,6-dihydro-2H-pyran-2-yl]-methanol

: 389860-58-6
(2R,5S,6R,1'E)-6-(but-1'-enyl)-5,6-dihydro-2-(p-methoxyphenoxy)-5-(tetrahydro-2''H-pyran-2''-yloxy)-2H-pyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -30 - 0 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: 4.50 g / tetrahydrofuran / -20 - 0 °C

3.1: 84 percent / DIBAL-H / diethyl ether / 1 h / -78 °C

4.1: 100 percent / pyridine / 1 h / 20 °C

5.1: 85.4 percent / Li₂CuCl₄ / tetrahydrofuran / 1 h / -8 °C

With pyridine; oxalyl dichloride; dilithium tetrachlorocuprate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Swern oxidation;
DOI:10.1039/b104341m