(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

Base Information

• Chemical Name: (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
• CAS No.: 204375-35-9
• Molecular Formula: C₃₄H₄₄O₃Si
• Molecular Weight: 528.807

Synonyms:(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

Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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: 70.0%

{(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetaldehyde (204375-34-8) → (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) + (2S,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

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide; for 8h; Ambient temperature;

DOI:10.1021/ja990215c

Reference yield: 70.0%

{(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetaldehyde (204375-34-8) → (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)

Guidance literature:

With chromium dichloride; nickel dichloride; In N,N-dimethyl-formamide;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/ja990215c

upstream raw materials:

{(1R,2R,6R)-2-[(S)-2-(5-Bromo-furan-2-yl)-2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-6-isopropyl-3-methyl-cyclohex-3-enyl}-acetaldehyde

(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

(1R,2R,6R)-6-Isopropyl-3-methyl-2-(2-oxo-ethyl)-cyclohex-3-enecarboxylic acid methyl ester

Downstream raw materials:

eleutherobin

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

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