(E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester
• CAS No.: 147058-98-8
• Molecular Formula: C₃₆H₄₈O₆Si
• Molecular Weight: 604.859

Synonyms:(E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester

Chemical Property of (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester

Chemical Property:

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Technology Process of (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester

There total 10 articles about (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic 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: 5.0%

(2R)-2-tert-butyl-5-methylene-1,3-dioxolan-4-one (130930-48-2) + ethyl 6-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-2(E),4(E),6(Z)-octatrienoate (146983-18-8) → (E)-3-[(2R,5S,6S,9R)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester (146983-25-7) + (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester (147058-98-8)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In acetonitrile; at 135 - 140 ℃; for 16h;

DOI:10.1021/jo00060a035

Reference yield:

methyl 2-(bromomethyl)-2-butenoate (33935-64-7) → (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester (147058-98-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaOAc, 2.) K₂CO₃ / 1.) MeOH, refluxed, 3 h, 2.) 25 deg C, 15 h

2: imidazole / dimethylformamide / 16 h / 25 °C

3: 92 percent / DIBAL-H / diethyl ether; hexane / 1 h / -50 °C

4: 96 percent / MnO₂ / CH₂Cl₂ / 48 h

5: 90 percent / CH₂Cl₂ / 16 h / Heating

6: 91 percent / DIBAL-H / diethyl ether; hexane / 1 h / -50 °C

7: 94 percent / MnO₂ / CH₂Cl₂ / 48 h

8: 1.) lithium hexamethyldisilazide / 1.) THF, -50 deg C, 15 min, 2.) THF, a) to 0 deg C over 2 h, b) 1 h

9: 5 percent / BHT / acetonitrile / 16 h / 135 - 140 °C

With 1H-imidazole; manganese(IV) oxide; 2,6-di-tert-butyl-4-methyl-phenol; sodium acetate; diisobutylaluminium hydride; potassium carbonate; lithium hexamethyldisilazane; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00060a035

Reference yield:

methyl 3-hydroxy-2-methylenebutyrate (98837-36-6,111002-28-9,112572-93-7,18020-65-0) → (E)-3-[(2R,5S,6R,9S)-2-tert-Butyl-8-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-4-oxo-1,3-dioxa-spiro[4.5]dec-7-en-6-yl]-2-methyl-acrylic acid ethyl ester (147058-98-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 91 percent / NBS, DMS / CH₂Cl₂ / 16 h / 25 °C

2: 1.) NaOAc, 2.) K₂CO₃ / 1.) MeOH, refluxed, 3 h, 2.) 25 deg C, 15 h

3: imidazole / dimethylformamide / 16 h / 25 °C

4: 92 percent / DIBAL-H / diethyl ether; hexane / 1 h / -50 °C

5: 96 percent / MnO₂ / CH₂Cl₂ / 48 h

6: 90 percent / CH₂Cl₂ / 16 h / Heating

7: 91 percent / DIBAL-H / diethyl ether; hexane / 1 h / -50 °C

8: 94 percent / MnO₂ / CH₂Cl₂ / 48 h

9: 1.) lithium hexamethyldisilazide / 1.) THF, -50 deg C, 15 min, 2.) THF, a) to 0 deg C over 2 h, b) 1 h

10: 5 percent / BHT / acetonitrile / 16 h / 135 - 140 °C

With 1H-imidazole; manganese(IV) oxide; N-Bromosuccinimide; 2,3-dimercapto-succinic acid; 2,6-di-tert-butyl-4-methyl-phenol; sodium acetate; diisobutylaluminium hydride; potassium carbonate; lithium hexamethyldisilazane; In diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00060a035

upstream raw materials:

(2R)-2-tert-butyl-5-methylene-1,3-dioxolan-4-one

ethyl 6-<<(tert-butyldiphenylsilyl)oxy>methyl>-2-methyl-2(E),4(E),6(Z)-octatrienoate

methyl 2-(bromomethyl)-2-butenoate

methyl 3-hydroxy-2-methylenebutyrate

Downstream raw materials:

methyl(1S,2S,5R)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-acetoxy-5-methyl-2-<2'-methyl-3'-<(tert-butyldimethylsilyl)oxy>-1'(E)-propen-1'-yl>-3-cyclohexene-1-carboxylate

methyl (1S,2R,5S)-4-<<(tert-butyldiphenylsilyl)oxy>methyl>-1-hydroxy-5-methyl-2-<2'-methyl-3'-<(tert-butyldimethylsilyl)oxy>-1'(E)-propen-1'-yl>-3-cyclohexene-1-carboxylate

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