3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

Base Information

Chemical Name:3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester
CAS No.:123886-94-2
Molecular Formula:C₂₀H₃₄O₅
Molecular Weight:354.487
Hs Code.:

Synonyms:3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

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Chemical Property of 3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

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Technology Process of 3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

There total 13 articles about 3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester 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: 100.0%

: 108-24-7
acetic anhydride

: 123886-93-1
ethyl 3-(5α-hydroxy-2,2,4α-trimethyl-3α-(3-oxobutyl)cyclohexan-1α-yl)propionate

: 123886-94-2
3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

Guidance literature:: In pyridine; for 4h; Ambient temperature;
DOI:10.1248/cpb.36.4722

Reference yield:

: 105631-37-6
methyl 3-(3,3-ethylenedioxybutyl)-2,4,4-trimethyl-5-oxo-3-cyclohexenecarboxylate

: 123886-94-2
3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

2: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

3: 100 percent / imidazole / dimethylformamide / 13 h / Ambient temperature

4: 1.5 g / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

5: 1.35 g / AcONa*3H₂O, PCC / CH₂Cl₂ / 2.5 h / Ambient temperature

6: toluene / 16 h / 100 °C

7: 851 mg / PtO₂/hydrogen / ethyl acetate / 0.5 h / Ambient temperature

8: 1.) p-toluenesulfonic acid / 1.) acetone, rt., 5 h; 2.) EtOH, 50 deg C, 5 h

9: 100 percent / pyridine / 4 h / Ambient temperature

With 1H-imidazole; platinum(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; hydrogen; sodium acetate; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In pyridine; methanol; diethyl ether; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;
DOI:10.1248/cpb.36.4722

Reference yield:

: 105631-36-5
2-ethylenedioxy-4-(2,6,6-trimethyl-5-nitromethyl-3-oxo-1-cyclohexen-1-yl)butane

: 123886-94-2
3-[(1S,3R,4S,5R)-5-Acetoxy-2,2,4-trimethyl-3-(3-oxo-butyl)-cyclohexyl]-propionic acid ethyl ester

Guidance literature:: Multi-step reaction with 13 steps

1: 88.4 percent / aq. 16percent titanium trichloride, AcONH₄, MeONa / H₂O; methanol / 0.33 h / Ambient temperature

2: 85.5 percent / Jones reagent / acetone / 0.5 h / 5 °C

3: 470 mg / K₂CO₃ / acetone / Heating

4: p-toluenesulfonic acid, Zeolite A-3 / benzene / 1 h / Heating

5: 63.9 percent / AcONa, hydrogen / 10percent Pd-C / ethyl acetate / 6 h / 73550.8 Torr / Ambient temperature

6: 84.1 percent / NaBH₄ / methanol / 1 h / -11 - -9 °C

7: 100 percent / imidazole / dimethylformamide / 13 h / Ambient temperature

8: 1.5 g / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

9: 1.35 g / AcONa*3H₂O, PCC / CH₂Cl₂ / 2.5 h / Ambient temperature

10: toluene / 16 h / 100 °C

11: 851 mg / PtO₂/hydrogen / ethyl acetate / 0.5 h / Ambient temperature

12: 1.) p-toluenesulfonic acid / 1.) acetone, rt., 5 h; 2.) EtOH, 50 deg C, 5 h

13: 100 percent / pyridine / 4 h / Ambient temperature

With 1H-imidazole; platinum(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; jones reagent; titanium(III) chloride; Zeolite A-3; ammonium acetate; hydrogen; sodium methylate; sodium acetate; potassium carbonate; toluene-4-sulfonic acid; pyridinium chlorochromate; palladium on activated charcoal; In pyridine; methanol; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; benzene;
DOI:10.1248/cpb.36.4722