(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

Base Information

Chemical Name:(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde
CAS No.:73198-39-7
Molecular Formula:C₁₉H₂₄O₃
Molecular Weight:300.398
Hs Code.:

Synonyms:(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

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Chemical Property of (1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

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Technology Process of (1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

There total 11 articles about (1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde 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: 90.0%

: (R)-4-((1R,4S,5R)-4-Benzyloxy-5-hydroxymethyl-5-methyl-cyclopent-2-enyl)-pentan-2-ol

: 73198-39-7
(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

Guidance literature:: With sodium acetate; pyridinium chlorochromate; In dichloromethane; for 0.5h; Ambient temperature;
DOI:10.1021/jo01299a043

Reference yield:

: 100-39-0
benzyl bromide

: 73198-39-7
(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) Na, HMPA, 2.) Tetra-n-butylammonium iodide / 1.) a) THF, 0 deg C, 15 min, b) room temp., 1 h, 2.) 50 deg C, 3 h

2: 96 percent / p-Toluenesulfonic acid / methanol / 1.) 1 h, 0 deg C, 2.) 4 h, room temp.

3: 100 percent / KOH / aq. ethanol / 18 h / Heating

4: 1.) p-Toluenesulfonyl chloride, 2.) 1,5-Diazabicyclo<5.4.0>undec-5-ene / 1.) Toluene, 0 deg C, 2.) a) 0 deg C, 15 min, b) 3 h, reflux

5: Diisobutylaluminium hydride / toluene / 0.25 h / -78 °C

6: 87 percent / benzene / 1 h / Ambient temperature

7: aq. HCl / tetrahydrofuran / 1 h / Ambient temperature

8: 62 percent / diethyl ether / 1.) -20 deg C, 2.) 0 deg C, 30 min

9: 90 percent / Pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 0.5 h / Ambient temperature

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; potassium hydroxide; sodium acetate; sodium; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; toluene-4-sulfonic acid; p-toluenesulfonyl chloride; pyridinium chlorochromate; 1,5-Diazabicyclo[5.4.0]undec-5-ene; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; benzene;
DOI:10.1021/jo01299a043

Reference yield:

: 73198-46-6
(R)-3-((1R,4S,5R)-4-Benzyloxy-5-hydroxymethyl-5-methyl-cyclopent-2-enyl)-butyraldehyde

: 73198-39-7
(1S,2S,5R)-2-Benzyloxy-1-methyl-5-((R)-1-methyl-3-oxo-butyl)-cyclopent-3-enecarbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1: 62 percent / diethyl ether / 1.) -20 deg C, 2.) 0 deg C, 30 min

2: 90 percent / Pyridinium chlorochromate, sodium acetate / CH₂Cl₂ / 0.5 h / Ambient temperature

With sodium acetate; pyridinium chlorochromate; In diethyl ether; dichloromethane;
DOI:10.1021/jo01299a043