(3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Base Information

• Chemical Name: (3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one
• CAS No.: 98974-34-6
• Molecular Formula: C₂₅H₃₈O₅SeSi
• Molecular Weight: 525.619
• Mol file: 98974-34-6.mol

Synonyms:

Chemical Property of (3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one

There total 1 articles about (3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-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: 86.0%

Phenylselenyl chloride (5707-04-0) + (3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (65025-95-8) → (3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (87224-46-2,98974-34-6)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)98135-8

Reference yield:

(3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (87224-46-2,98974-34-6) → Benzoic acid 2-[(1R,2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1,5-dihydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethyl ester (98892-08-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / 10percent aq. H₂O₂ / CH₂Cl₂ / 1 h / Heating

2: 86 percent / diisobutylaluminium hydride / toluene / 0.5 h / 0 °C

3: 83 percent / t-BuOOH / Vanadium

4: 60 percent / Red-Al / tetrahydrofuran / 0.5 h / 0 °C

5: 66 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

With pyridine; tert.-butylhydroperoxide; dihydrogen peroxide; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; vanadium; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/S0040-4039(00)98135-8

Reference yield:

(3aR,4S,5R,6aS)-4-(tert-Butyl-dimethyl-silanyloxymethyl)-3-phenylselanyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one (87224-46-2,98974-34-6) → Benzoic acid 2-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethyl ester (98892-10-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 79 percent / 10percent aq. H₂O₂ / CH₂Cl₂ / 1 h / Heating

2: 86 percent / diisobutylaluminium hydride / toluene / 0.5 h / 0 °C

3: 83 percent / t-BuOOH / Vanadium

4: 60 percent / Red-Al / tetrahydrofuran / 0.5 h / 0 °C

5: 66 percent / pyridine / CH₂Cl₂ / 1 h / -20 °C

6: 90 percent / imidazole / dimethylformamide / 18 h / 25 °C

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dihydrogen peroxide; diisobutylaluminium hydride; sodium bis(2-methoxyethoxy)aluminium dihydride; vanadium; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(00)98135-8

upstream raw materials:

Phenylselenyl chloride

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

5E,7E-Clavulone II

Benzoic acid 2-[(1R,2S,3R,5S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1,5-dihydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethyl ester

Benzoic acid 2-[(1R,2S,3R,5S)-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-1-hydroxy-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethyl ester

5E,7Z-Clavulone III