2-Cyclohexen-1-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4-hydroxy-, (4R)-

Base Information

• Chemical Name: 2-Cyclohexen-1-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4-hydroxy-, (4R)-
• CAS No.: 877052-52-3
• Molecular Formula: C13H24O3Si
• Molecular Weight: 256.417
• Mol file: 877052-52-3.mol

Synonyms:

Chemical Property of 2-Cyclohexen-1-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4-hydroxy-, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclohexen-1-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4-hydroxy-, (4R)-

There total 5 articles about 2-Cyclohexen-1-one, 4-[[[(1,1-dimethylethyl)dimethylsilyl]oxy]methyl]-4-hydroxy-, (4R)- 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:

(R)-7-(N-phenyl-aminooxy)-2,3-dioxa-spiro[4.5]decan-8-one (682746-13-0) → 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-cyclohex-2-enone (877052-52-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 90 percent / H₂ / Pd/C / tetrahydrofuran / 3 h

2: 68 percent / Et₃N / 2.5 h / 0 °C

3: 72 percent / DIBAL-H / diethyl ether / -60 - -30 °C

4: DIBAL-H / CH₂Cl₂ / 0.33 h / -50 - -30 °C

5: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C

6: Et₃N; DMAP / CH₂Cl₂

With dmap; Amberlyst 15; hydrogen; diisobutylaluminium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/anie.200502826

Reference yield:

(R)-4-hydroxy-1,4-dioxa-spiro[4.5]decan-8-one (851764-31-3) → 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-cyclohex-2-enone (877052-52-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / Et₃N / 2.5 h / 0 °C

2: 72 percent / DIBAL-H / diethyl ether / -60 - -30 °C

3: DIBAL-H / CH₂Cl₂ / 0.33 h / -50 - -30 °C

4: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C

5: Et₃N; DMAP / CH₂Cl₂

With dmap; Amberlyst 15; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1002/anie.200502826

Reference yield:

(7R,8R)-7,8-Bis-trimethylsilanyloxy-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde (877052-51-2) → 4-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-cyclohex-2-enone (877052-52-3)

Guidance literature:

Multi-step reaction with 3 steps

1: DIBAL-H / CH₂Cl₂ / 0.33 h / -50 - -30 °C

2: Amberlyst 15 / tetrahydrofuran / 48 h / 60 °C

3: Et₃N; DMAP / CH₂Cl₂

With dmap; Amberlyst 15; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1002/anie.200502826

upstream raw materials:

(R)-4-hydroxy-1,4-dioxa-spiro[4.5]decan-8-one

(7R,8R)-7,8-Bis-trimethylsilanyloxy-1,4-dioxa-spiro[4.5]decane-8-carbaldehyde

(7R,8S)-7,8-Bis-trimethylsilanyloxy-1,4-dioxa-spiro[4.5]decane-8-carbonitrile

(R)-7-(N-phenyl-aminooxy)-2,3-dioxa-spiro[4.5]decan-8-one

Downstream raw materials:

FR65814

fumagillol

Toluene-4-sulfonic acid (1R,2S,3S)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-1,3-dihydroxy-4-oxo-cyclohexylmethyl ester

(1R,2R)-1-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((E)-1,5-dimethyl-hexa-1,4-dienyl)-4-trimethylsilanyloxy-cyclohex-3-enol

Refernces