6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Base Information

• Chemical Name: 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one
• CAS No.: 482315-17-3
• Molecular Formula: C₃₆H₅₇NO₆Si
• Molecular Weight: 627.937
• Mol file: 482315-17-3.mol

Synonyms:6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Chemical Property of 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

There total 13 articles about 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-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: 80.0%

2-hexyl-2-(6-iodohexyl)-1,3-dioxolane (482315-11-7) + 6-[1-(tert-butyl-dimethyl-silanyloxy)-3-iodo-allyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one (482315-10-6) → 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one (482315-17-3)

Guidance literature:

2-hexyl-2-(6-iodohexyl)-1,3-dioxolane; With tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 ℃; for 0.25h;

6-[1-(tert-butyl-dimethyl-silanyloxy)-3-iodo-allyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one; With zinc(II) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; pentane; at 20 ℃; for 3h; Further stages.;

DOI:10.1021/ol020164f

Reference yield:

C20H31NO4Si (482315-16-2) → 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one (482315-17-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 75 percent / K₂CO₃ / Pd(PPh₃)4 / acetonitrile / 24 h / Heating

2.1: 99 percent / TBAF / tetrahydrofuran

3.1: RuCl₃; potassium persulfate; potassium hydroxide / H₂O / 7 h

4.1: 252 mg / diethyl ether

5.1: KHMDS; HMPA / tetrahydrofuran / 0.33 h / -78 °C

5.2: 73 percent / tetrahydrofuran / 3 h / -78 °C

6.1: O₃ / methanol / -78 °C

6.2: DMS / methanol

7.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.5 h / -20 °C

7.2: 78 percent / CH₂Cl₂ / 3 h / 25 °C

8.1: O₃ / methanol / -78 °C

8.2: DMS / methanol

9.1: 367 mg / CrCl₂ / tetrahydrofuran / 0.5 h

10.1: tert-butyllithium / pentane; tetrahydrofuran / 0.25 h / -78 °C

10.2: 80 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran; pentane / 3 h / 20 °C

With chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; potassium carbonate; ozone; magnesium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; pentane;

DOI:10.1021/ol020164f

Reference yield:

N-[2-(tert-butyl-dimethyl-silanyloxy)-1-formyl-ethyl]-benzamide (503560-10-9) → 6-[1-(tert-butyl-dimethyl-silanyloxy)-9-(2-hexyl-[1,3]dioxolan-2-yl)-non-2-enyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one (482315-17-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 2.52 g / tetrahydrofuran / 1 h / 20 °C

2.1: 389 mg / pyridine / CH₂Cl₂ / 12 h

3.1: 75 percent / K₂CO₃ / Pd(PPh₃)4 / acetonitrile / 24 h / Heating

4.1: 99 percent / TBAF / tetrahydrofuran

5.1: RuCl₃; potassium persulfate; potassium hydroxide / H₂O / 7 h

6.1: 252 mg / diethyl ether

7.1: KHMDS; HMPA / tetrahydrofuran / 0.33 h / -78 °C

7.2: 73 percent / tetrahydrofuran / 3 h / -78 °C

8.1: O₃ / methanol / -78 °C

8.2: DMS / methanol

9.1: MgBr₂*OEt₂ / CH₂Cl₂ / 0.5 h / -20 °C

9.2: 78 percent / CH₂Cl₂ / 3 h / 25 °C

10.1: O₃ / methanol / -78 °C

10.2: DMS / methanol

11.1: 367 mg / CrCl₂ / tetrahydrofuran / 0.5 h

12.1: tert-butyllithium / pentane; tetrahydrofuran / 0.25 h / -78 °C

12.2: 80 percent / ZnCl₂ / Pd(PPh₃)4 / tetrahydrofuran; pentane / 3 h / 20 °C

With pyridine; chromium dichloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ruthenium trichloride; potassium hydroxide; potassium peroxomonosulphate; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium hexamethylsilazane; potassium carbonate; ozone; magnesium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetonitrile; pentane; 1.1: Grignard reaction;

DOI:10.1021/ol020164f

upstream raw materials:

2-hexyl-2-(6-iodohexyl)-1,3-dioxolane

6-[1-(tert-butyl-dimethyl-silanyloxy)-3-iodo-allyl]-3a-methyl-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

C₂₀H₃₁NO₄Si

(4S,trans)-4,5-dihydro-4-(tert-butyldimethylsilanyloxymethyl)-2-phenyloxazoline

Downstream raw materials:

sphingofungin F

Refernces