2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester
• CAS No.: 204375-36-0
• Molecular Formula: C₃₉H₅₂O₄Si
• Molecular Weight: 612.925

Synonyms:2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester

Chemical Property:

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Technology Process of 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl ester

There total 12 articles about 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-yl 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: 91.0%

pivaloyl chloride (3282-30-2) + (2R,4R,5R,9R,11S)-11-(tert-Butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-1(14),7,12-trien-2-ol (204375-35-9) → 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-1(14),7,12-trien-2-yl ester (204375-36-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 5h;

DOI:10.1021/ja990215c

Reference yield:

{(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-methanol (204375-23-5) → 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-1(14),7,12-trien-2-yl ester (204375-36-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / pyridine, DMAP / 4 h / 25 °C

2: 96 percent / 18-crown-6 / acetonitrile / 2.5 h / 60 °C

3: 86 percent / DIBAL / toluene; hexane / 1 h / -78 - 20 °C

4: 70 percent / CrCl₂, NiCl₂ / dimethylformamide / 8 h / Ambient temperature

5: 91 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

With pyridine; chromium dichloride; dmap; 18-crown-6 ether; diisobutylaluminium hydride; triethylamine; nickel dichloride; In hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/ja990215c

Reference yield:

{(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetonitrile (204375-25-7) → 2,2-Dimethyl-propionic acid (2R,4R,5R,9R,11S)-11-(tert-butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.04,9]pentadeca-1(14),7,12-trien-2-yl ester (204375-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / DIBAL / toluene; hexane / 1 h / -78 - 20 °C

2: 70 percent / CrCl₂, NiCl₂ / dimethylformamide / 8 h / Ambient temperature

3: 91 percent / DMAP, Et₃N / CH₂Cl₂ / 5 h

With chromium dichloride; dmap; diisobutylaluminium hydride; triethylamine; nickel dichloride; In hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja990215c

upstream raw materials:

pivaloyl chloride

(2R,4R,5R,9R,11S)-11-(tert-Butyl-diphenyl-silanyloxy)-5-isopropyl-8-methyl-15-oxa-tricyclo[10.2.1.0^4,9]pentadeca-1⁽¹⁴⁾,7,12-trien-2-ol

(1R,5R,6R)-5-Isopropyl-2-methyl-bicyclo[4.2.0]oct-2-en-7-one

(1R,5R,6R)-8-[1-Dimethylamino-meth-(E)-ylidene]-5-isopropyl-2-methyl-bicyclo[4.2.0]oct-2-en-7-one

Downstream raw materials:

eleutherobin

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