7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene

Base Information

• Chemical Name: 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene
• CAS No.: 137445-65-9
• Molecular Formula: C₃₉H₅₄O₃Si₂
• Molecular Weight: 627.027
• Mol file: 137445-65-9.mol

Synonyms:

Chemical Property of 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene

There total 13 articles about 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene 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:

(dibromomethyl)trimethylsilane (2612-42-2) + (E)-(R)-3-(tert-Butyl-diphenyl-silanyloxymethyl)-8-(5,9-dihydro-6,8-dioxa-benzocyclohepten-7-yl)-2-methyl-oct-4-enal → 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene (137445-65-9,137445-72-8)

Guidance literature:

With chromium dichloride; In tetrahydrofuran; at 50 ℃; Yield given; ultrasound;

DOI:10.1016/S0040-4039(00)92272-X

Reference yield:

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) → 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene (137445-65-9,137445-72-8)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent

2: 72 percent / PCC, 3 Angstroem mol. sieves, Celite / CH₂Cl₂ / 25 °C

3: 93 percent / PPTS / benzene / Heating

4: (S)-BINAL-H / tetrahydrofuran / -100 - -78 °C

5: 100 percent / Bu₄NF / tetrahydrofuran / 25 °C

6: 97 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 0 - 25 °C

7: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

8: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

9: 1) LDA, 2) HMPA, t-BuMe₂SiCl / 1) THF, -78 deg C, 2) -78 deg C - 25 deg C

10: diethyl ether / 25 °C

11: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

12: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) CH₂Cl₂, -60 deg C, 2) 60 deg C to 25 deg C

13: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; (-)-(S)-BINAL-H; 3 A molecular sieve; Celite; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)92272-X

Reference yield:

(E)-(S)-7-(5,9-Dihydro-6,8-dioxa-benzocyclohepten-7-yl)-hept-2-ene-1,4-diol → 7-[(4E,8E)-(R)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-9-trimethylsilanyl-nona-4,8-dienyl]-5,9-dihydro-6,8-dioxa-benzocycloheptene (137445-65-9,137445-72-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

2: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

3: 1) LDA, 2) HMPA, t-BuMe₂SiCl / 1) THF, -78 deg C, 2) -78 deg C - 25 deg C

4: diethyl ether / 25 °C

5: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

6: 1) (COCl)2, DMSO, 2) N(Et)3 / 1) CH₂Cl₂, -60 deg C, 2) 60 deg C to 25 deg C

7: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

With pyridine; 1H-imidazole; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; oxalyl dichloride; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)92272-X

upstream raw materials:

(dibromomethyl)trimethylsilane

3,4,5,6-tetrahydro-2H-pyran-2-one

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one

Propionic acid (E)-(S)-4-(tert-butyl-diphenyl-silanyloxy)-1-[3-(5,9-dihydro-6,8-dioxa-benzocyclohepten-7-yl)-propyl]-but-2-enyl ester

Downstream raw materials:

(+)-dihydrocompactin

(1S,7S,8S,8aR)-8-(tert-Butyl-diphenyl-silanyloxymethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol

(1S,4aS,5S,6S,7R,8R,8aR)-5,6-Dibromo-8-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-naphthalen-1-ol

(R)-3-Hydroxy-7-[(1S,2S,4aR,8S,8aS)-2-methyl-8-((S)-2-methyl-butyryloxy)-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-1-yl]-5-oxo-heptanoic acid 4-nitro-phenyl ester