(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

Base Information

Chemical Name:(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone
CAS No.:89471-92-1
Molecular Formula:C₂₄H₃₄O₂
Molecular Weight:354.533
Hs Code.:

Synonyms:(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

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Chemical Property of (2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

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Technology Process of (2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

There total 12 articles about (2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone 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: 59.0%

: 89471-91-0
(2R,3R)-3-((E)-(R)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-1-(1-ethoxy-ethoxy)-2-methyl-cyclopentanecarbonitrile

: 89471-92-1
(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

Guidance literature:: With potassium hydroxide; toluene-4-sulfonic acid; In methanol;
DOI:10.1016/S0040-4039(00)88931-5

Reference yield:

: 63473-89-2
triethyl orthohexenate

: 89471-92-1
(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

Guidance literature:: Multi-step reaction with 7 steps

1: 70 percent / 1 h / 140 °C

3: 80 percent / KN(SiMe₃)2 / tetrahydrofuran / -25 °C

4: i-Bu₂AlH / tetrahydrofuran / 0 °C

5: 2.) pyridinium chlorochromate / 1.) pyridine, -20 deg C, 2.) CH₂Cl₂

7: 59 percent / p-TsOH, 2percent aqueous KOH / methanol

With potassium hydroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)88931-5

Reference yield:

: 5048-19-1
hex-5-enenitrile

: 89471-92-1
(2S,3S)-3-((E)-(S)-3-Benzyloxy-5-methyl-hex-1-enyl)-2-but-3-enyl-2-methyl-cyclopentanone

Guidance literature:: Multi-step reaction with 8 steps

1: 1.)HCl, / 1.) Et₂O, 2 days, 0 deg C, 2.) Et₂O, 3 days, 25 deg C,

2: 70 percent / 1 h / 140 °C

4: 80 percent / KN(SiMe₃)2 / tetrahydrofuran / -25 °C

5: i-Bu₂AlH / tetrahydrofuran / 0 °C

6: 2.) pyridinium chlorochromate / 1.) pyridine, -20 deg C, 2.) CH₂Cl₂

8: 59 percent / p-TsOH, 2percent aqueous KOH / methanol

With hydrogenchloride; potassium hydroxide; potassium hexamethylsilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In tetrahydrofuran; methanol;
DOI:10.1016/S0040-4039(00)88931-5