(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

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Chemical Name:(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one
CAS No.:261357-51-1
Molecular Formula:C₂₆H₃₈O₅
Molecular Weight:430.585
Hs Code.:

Synonyms:(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

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Chemical Property of (5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

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Technology Process of (5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

There total 13 articles about (5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-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:

: 90645-95-7
4-methyl-3-(methylethyl)pent-2-enal

: 261357-51-1
(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / H₂ / 10percent Pd/C / CH₂Cl₂ / 12 h / 20 °C / 2120.36 Torr

2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

2.2: 89 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

3.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; dichloromethane; 1.1: Catalytic hydrogenation / 2.1: Metallation / 2.2: Addition / 3.1: mesylation / 4.1: Elimination;
DOI:10.1021/jm9904607

Reference yield:

: (S)-2-((S)-2-Benzyloxy-1-hydroxy-ethyl)-5-oxo-tetrahydro-furan-2-carbaldehyde

: 261357-51-1
(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium borohydride / methanol / 0 °C

2.1: 99 percent / H₂; AcOH / 10percent Pd/C / methanol / 5 h

3.1: 97 percent / p-toluenesulfonic acid / 4 h / 20 °C

4.1: 84 percent / silver(I) oxide / dimethylformamide / 96 h / 20 °C

5.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

5.2: 89 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With sodium tetrahydroborate; hydrogen; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver(l) oxide; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 2.1: Hydrogenolysis / 3.1: ketalization / 4.1: Alkylation / 5.1: Metallation / 5.2: Addition / 6.1: mesylation / 7.1: Elimination;
DOI:10.1021/jm9904607

Reference yield:

: 261357-48-6
(5R)-5-(hydroxymethyl)-5-[(1S)-1-hydroxy-2-(phenylmethoxy)ethyl]oxolan-2-one

: 261357-51-1
(5R)-5-[(1S)-3,3-dimethyl(2,4-dioxolanyl)]-3-[(E)-4-methyl-3-(methylethyl)pentylidene]-5-[(phenylmethoxy)methyl]oxolan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 99 percent / H₂; AcOH / 10percent Pd/C / methanol / 5 h

2.1: 97 percent / p-toluenesulfonic acid / 4 h / 20 °C

3.1: 84 percent / silver(I) oxide / dimethylformamide / 96 h / 20 °C

4.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 0.5 h / -78 °C

4.2: 89 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: Et₃N / CH₂Cl₂ / 2.5 h / 0 - 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

With hydrogen; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; silver(l) oxide; lithium hexamethyldisilazane; 10percent Pd/C; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Hydrogenolysis / 2.1: ketalization / 3.1: Alkylation / 4.1: Metallation / 4.2: Addition / 5.1: mesylation / 6.1: Elimination;
DOI:10.1021/jm9904607