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

Base Information

• Chemical Name: 1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one
• CAS No.: 137445-61-5
• Molecular Formula: C₂₄H₃₀O₃Si
• Molecular Weight: 394.586
• Mol file: 137445-61-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about 1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-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: 99.0%

3,4,5,6-tetrahydro-2H-pyran-2-one (542-28-9,26354-94-9) + tert-butyl(diphenyl)(2-propynyloxy)silane (110824-26-5) → 1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one (137445-61-5)

Guidance literature:

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

Reference yield: 72.0%

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one (137445-61-5) → 8-(tert-Butyl-diphenyl-silanyloxy)-5-oxo-oct-6-ynal

Guidance literature:

With 3 A molecular sieve; Celite; pyridinium chlorochromate; In dichloromethane; at 25 ℃;

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

Reference yield:

1-(tert-Butyl-diphenyl-silanyloxy)-8-hydroxy-oct-2-yn-4-one (137445-61-5) → (1S,4aS,5S,6S,7R,8R,8aR)-5,6-Dibromo-8-(tert-butyl-diphenyl-silanyloxymethyl)-7-methyl-decahydro-naphthalen-1-ol (137445-71-7)

Guidance literature:

Multi-step reaction with 17 steps

1: 72 percent / PCC, 3 Angstroem mol. sieves, Celite / CH₂Cl₂ / 25 °C

2: 93 percent / PPTS / benzene / Heating

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

4: 100 percent / Bu₄NF / tetrahydrofuran / 25 °C

5: 97 percent / sodium bis(2-methoxyethoxy)aluminum hydride / tetrahydrofuran / 0 - 25 °C

6: 93 percent / imidazole / dimethylformamide; CH₂Cl₂ / 0 - 25 °C

7: 97 percent / pyridine / CH₂Cl₂ / 0 - 25 °C

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

9: diethyl ether / 25 °C

10: 91 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

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

12: CrCl₂ / tetrahydrofuran / 50 °C / ultrasound

13: TiCl₄ / CH₂Cl₂ / -78 °C

14: 95 percent / Bu₄NF / tetrahydrofuran / 25 °C

15: 97 percent / Na/NH₃ / tetrahydrofuran / -78 °C

16: 86 percent / imidazole / CH₂Cl₂ / 0 - 25 °C

17: 97 percent / Br₂ / CCl₄; diethyl ether / -60 - -10 °C

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; ammonia; bromine; sodium; pyridinium p-toluenesulfonate; titanium tetrachloride; diisobutylaluminium hydride; tert-butyldimethylsilyl chloride; dimethyl sulfoxide; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene;

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

upstream raw materials:

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

tert-butyl(diphenyl)(2-propynyloxy)silane

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

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