(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

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Chemical Name:(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one
CAS No.:208713-60-4
Molecular Formula:C₂₁H₃₀O₄
Molecular Weight:346.467
Hs Code.:

Synonyms:(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

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Chemical Property of (E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

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Technology Process of (E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

There total 10 articles about (E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one 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: 78.0%

: 208713-59-1
(E)-4-[(2R,3R,4S,6R)-6-Butyl-3-methoxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-2-methyl-1-phenyl-but-2-en-1-one

: 208713-60-4
(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; for 20h; Heating;
DOI:10.1080/07328309808002895

Reference yield:

: 84010-40-2
(2R-(2α,3β,6β))-6-Butyl-2-({[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl)tetrahydro-3-methoxy-4H-pyran-4-one

: 208713-60-4
(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

Guidance literature:: Multi-step reaction with 11 steps

1: 99 percent / NaBH₄ / methanol / 2 h / 0 °C

2: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

3: 4.261 g / tetra-n-butyammonium fluoride / tetrahydrofuran / 1) ice-bath, 5 min; 2) rt, 1 h

4: 81 percent / pyridine / 19 h / -22 °C

5: 81 percent / NaI, K₂CO₃ / acetone / 24 h / Heating

6: 1.) n-BuLi / 1) hexane, THF, -78 deg C, 10 min, -78 --> 0 deg C, 13 min; 2) hexane, THF, -78 deg C, 2 min, -78 deg C --> rt, 1.5 h

7: 1.) m-chloroperbenzoic acid, 2.) Et₂NH / 1) CH₂Cl₂, 0.5 h; 2) CH₂Cl₂, CH₃OH, rt, 18 h

8: 1.578 g / MnO₂ / benzene / 24 h / Ambient temperature

9: 98 percent / diethyl ether / 2 h

10: MnO₂ / benzene / 4 h / Ambient temperature

11: 78 percent / pyridinium p-toluenesulfonate / aq. ethanol / 20 h / Heating

With pyridine; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; diethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; acetone; benzene;
DOI:10.1080/07328309808002895

Reference yield:

: 208713-53-5
(2R,3S,4S,6R)-6-Butyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxy-tetrahydro-pyran-4-ol

: 208713-60-4
(E)-4-((2R,3S,4S,6R)-6-Butyl-4-hydroxy-3-methoxy-tetrahydro-pyran-2-yl)-2-methyl-1-phenyl-but-2-en-1-one

Guidance literature:: Multi-step reaction with 10 steps

1: 99 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 16 h / Ambient temperature

2: 4.261 g / tetra-n-butyammonium fluoride / tetrahydrofuran / 1) ice-bath, 5 min; 2) rt, 1 h

3: 81 percent / pyridine / 19 h / -22 °C

4: 81 percent / NaI, K₂CO₃ / acetone / 24 h / Heating

5: 1.) n-BuLi / 1) hexane, THF, -78 deg C, 10 min, -78 --> 0 deg C, 13 min; 2) hexane, THF, -78 deg C, 2 min, -78 deg C --> rt, 1.5 h

6: 1.) m-chloroperbenzoic acid, 2.) Et₂NH / 1) CH₂Cl₂, 0.5 h; 2) CH₂Cl₂, CH₃OH, rt, 18 h

7: 1.578 g / MnO₂ / benzene / 24 h / Ambient temperature

8: 98 percent / diethyl ether / 2 h

9: MnO₂ / benzene / 4 h / Ambient temperature

10: 78 percent / pyridinium p-toluenesulfonate / aq. ethanol / 20 h / Heating

With pyridine; manganese(IV) oxide; n-butyllithium; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; potassium carbonate; diethylamine; 3-chloro-benzenecarboperoxoic acid; sodium iodide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; acetone; benzene;
DOI:10.1080/07328309808002895