(Z)-neomanoalide

Base Information

• Chemical Name: (Z)-neomanoalide
• CAS No.: 112572-49-3
• Molecular Formula: C₂₅H₃₈O₄
• Molecular Weight: 402.574
• Mol file: 112572-49-3.mol

Synonyms:

Chemical Property of (Z)-neomanoalide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-neomanoalide

There total 19 articles about (Z)-neomanoalide 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:

4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[(2E,6E)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl]-5H-furan-2-one (158413-25-3) → (E)-neomanoalide (112572-49-3)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 2.5h; Yield given;

DOI:10.1016/S0040-4039(00)95323-1

Reference yield:

2-((3E,7Z)-9-Chloro-7-dimethoxymethyl-3-methyl-nona-3,7-dienyl)-1,3,3-trimethyl-cyclohexene (112503-50-1) → (E)-neomanoalide (112572-49-3)

Guidance literature:

Multi-step reaction with 7 steps

1: palladium dibenzylidenacetone, Ph₃P / 12 h / 50 °C

2: 2N HCl / tetrahydrofuran / 2 h / 0 °C

3: DIBAL

5: Singlet oxygen

6: NaBH₄ / ethanol / 0 °C

7: 2N HCl / tetrahydrofuran / 2.5 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; (dibenzylideneacetone)palladium; oxygen; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(00)95323-1

Reference yield:

2-trimethylsilyl-4-hydroxymethyl-5-tributyl-stannylfuran (112503-51-2) → (E)-neomanoalide (112572-49-3)

Guidance literature:

Multi-step reaction with 7 steps

1: palladium dibenzylidenacetone, Ph₃P / 12 h / 50 °C

2: 2N HCl / tetrahydrofuran / 2 h / 0 °C

3: DIBAL

5: Singlet oxygen

6: NaBH₄ / ethanol / 0 °C

7: 2N HCl / tetrahydrofuran / 2.5 h / 0 °C

With hydrogenchloride; sodium tetrahydroborate; (dibenzylideneacetone)palladium; oxygen; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(00)95323-1

upstream raw materials:

4-(tert-Butyl-dimethyl-silanyloxymethyl)-5-[(2E,6E)-3-(tert-butyl-dimethyl-silanyloxymethyl)-7-methyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,6-dienyl]-5H-furan-2-one

Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate

(E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-en-1-ol

(E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-enyl)pent-2-enyl bromide

Downstream raw materials:

seco-manoalide

(E)-2-[2-(3-Hydroxymethyl-5-oxo-2,5-dihydro-furan-2-yl)-eth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-enal

Acetic acid (E)-2-[2-(3-acetoxymethyl-5-oxo-2,5-dihydro-furan-2-yl)-eth-(Z)-ylidene]-6-methyl-8-(2,6,6-trimethyl-cyclohex-1-enyl)-oct-5-enyl ester