3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one

Base Information

• Chemical Name: 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one
• CAS No.: 80558-55-0
• Molecular Formula: C₃₂H₄₄O₅Si
• Molecular Weight: 536.784
• Mol file: 80558-55-0.mol

Synonyms:3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one

Chemical Property of 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one

There total 23 articles about 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-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: 92.0%

cyclohexanone (108-94-1,11119-77-0,9003-41-2,9075-99-4) + <5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2α,3β,4β,5α-tetrahydro-3,4-dihydroxy-2H-pyran-2-yl>-2-propanone (86611-21-4) → 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one (80558-55-0)

Guidance literature:

With toluene-4-sulfonic acid; copper(II) sulfate; In benzene; at 25 ℃; for 15h;

DOI:10.1021/jo00166a013

Reference yield:

5α-<2-ethyl>-5,6-dihydro-2H-pyran-2α-ylpropan-2-ol (86611-19-0,86611-20-3) → 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one (80558-55-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / pyridinium chlorochromate / CH₂Cl₂ / 4 h

2: OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 27 h / Heating

3: 144 mg / CuSO₄, TsOH / benzene / 0.83 h / Ambient temperature

With osmium(VIII) oxide; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; pyridinium chlorochromate; In dichloromethane; tert-butyl alcohol; benzene;

Reference yield:

5α-<2-ethyl>-5,6-dihydro-2H-pyran-2α-ylpropan-2-one (80502-35-8) → 3β,4β-cyclohexylidenedioxy-5α-<2-ethyl>tetrahydro-2H-pyran-2α-ylpropan-2-one (80558-55-0)

Guidance literature:

Multi-step reaction with 2 steps

1: OsO₄, N-methylmorpholine N-oxide / 2-methyl-propan-2-ol / 27 h / Heating

2: 144 mg / CuSO₄, TsOH / benzene / 0.83 h / Ambient temperature

With osmium(VIII) oxide; toluene-4-sulfonic acid; copper(II) sulfate; 4-methylmorpholine N-oxide; In tert-butyl alcohol; benzene;

upstream raw materials:

cyclohexanone

<5-(2-((tert-butyldiphenylsilyl)oxy)ethyl)-2α,3β,4β,5α-tetrahydro-3,4-dihydroxy-2H-pyran-2-yl>-2-propanone

tert-butylchlorodiphenylsilane

1-triphenylphosphoranylidene-2-propanone

Downstream raw materials:

C₂₀H₃₂O₆

C₃₆H₅₀O₆Si

C₃₆H₅₀O₆Si