(3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde

Base Information

• Chemical Name: (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde
• CAS No.: 85785-69-9
• Molecular Formula: C₂₁H₃₂O₄
• Molecular Weight: 348.483
• Mol file: 85785-69-9.mol

Synonyms:

Chemical Property of (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde

There total 3 articles about (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde 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:

(E)-tetrahydro-2-<(3-methyl-2-penten-4-ynyl)oxy>-2H-pyran (41967-81-1,58389-95-0,61568-79-4,134079-53-1) → (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde (85785-69-9,94346-64-2,94347-28-1)

Guidance literature:

Multi-step reaction with 3 steps

2: NaH / benzene / 10 °C

3: 1, LDA / 1, THF, -20 degg 2, THF-HMPA

With sodium hydride; lithium diisopropyl amide; In benzene;

DOI:10.1016/0040-4039(82)80152-4

Reference yield:

3,4-dimethyl-cyclohex-2-enone (10463-42-0) → (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde (85785-69-9,94346-64-2,94347-28-1)

Guidance literature:

Multi-step reaction with 3 steps

2: NaH / benzene / 10 °C

3: 1, LDA / 1, THF, -20 degg 2, THF-HMPA

With sodium hydride; lithium diisopropyl amide; In benzene;

DOI:10.1016/0040-4039(82)80152-4

Reference yield:

(4R,5R)-4,5-Dimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde (85785-68-8,94346-63-1,94347-27-0) + methyl iodide (74-88-4) → (3R,4R,5R)-3,4,5-Trimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde (85785-69-9,94346-64-2,94347-28-1)

Guidance literature:

With lithium diisopropyl amide; Multistep reaction; 1, THF, -20 degg 2, THF-HMPA;

DOI:10.1016/0040-4039(82)80152-4

upstream raw materials:

(4R,5R)-4,5-Dimethyl-4-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-2-oxo-cyclohexanecarbaldehyde

methyl iodide

(E)-tetrahydro-2-<(3-methyl-2-penten-4-ynyl)oxy>-2H-pyran

3,4-dimethyl-cyclohex-2-enone

Downstream raw materials:

(2S,3S,4S)-2,3,4-Trimethyl-3-[(1E,3E)-3-methyl-5-(tetrahydro-pyran-2-yloxy)-penta-1,3-dienyl]-cyclohexanone

(+/-) ascochlorin

(+/-)-(2'E,4'E)-3-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>-1,5-dichloro-6-methyl-2,4-cyclohexanedione

(+/-)-(2'E,4'E)-4-chloro-2-<5'-(3,3-ethylenedioxy-1,2,6-trimethylcyclohexyl)-3'-methyl-2',4'-pentadienyl>orcinol