(+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

Base Information

• Chemical Name: (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione
• CAS No.: 913071-27-9
• Molecular Formula: C₃₂H₅₅NO₅Si₃
• Molecular Weight: 618.049
• Mol file: 913071-27-9.mol

Synonyms:(+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

Chemical Property of (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

There total 4 articles about (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione 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: 78.0%

(-)-2-((1R,4S,5R,6R)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione (913071-23-5) + triethylsilyl chloride (994-30-9) → (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione (913071-27-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 15h;

DOI:10.1016/j.bmc.2006.05.080

Reference yield:

(+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[tert-butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione (913071-20-2) → (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione (913071-27-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / p-toluenesulfonic acid / methanol / 0.75 h / 65 °C

2: 78 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; In methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2006.05.080

Reference yield:

(1S,4S,5R,6R)-4,5,6-Tris-(tert-butyl-dimethyl-silanyloxy)-cyclohex-2-enol → (+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione (913071-27-9)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl azodicarboxylate; PPh₃ / toluene / 6 h / 0 °C

2: 91 percent / p-toluenesulfonic acid / methanol / 0.75 h / 65 °C

3: 78 percent / imidazole / dimethylformamide / 15 h / 20 °C

With 1H-imidazole; toluene-4-sulfonic acid; triphenylphosphine; diethylazodicarboxylate; In methanol; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.bmc.2006.05.080

upstream raw materials:

(-)-2-((1R,4S,5R,6R)-4,5,6-trihydroxycyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

triethylsilyl chloride

(+)-2-((1R,4S,5R,6R)-4,5,6-tris-{[tert-butyl(dimethyl)silyl]oxy}cyclohex-2-en-1-yl)-1H-isoindole-1,3(2H)-dione

phthalimide

Downstream raw materials:

(+)-(1R,4S,5R,6R)-4,5,6-tris-{[triethylsilyl]oxy}cyclohex-2-ene-1-amine