seco-manoalide

Base Information

• Chemical Name: seco-manoalide
• CAS No.: 105498-76-8
• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.558

Synonyms:seco-manoalide

Chemical Property of seco-manoalide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

SDS file from LookChem

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Technology Process of seco-manoalide

There total 38 articles about seco-manoalide 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: 40.0%

3-<(1R,S)-(3E,7E)-<10-(2,6,6-trimethyl-1-cyclohexen-1-yl)-8-methyl-4-formyl-1-hydroxy>-3,7-decadien-1-yl>furan (160084-22-0) → seco-manoalide (105498-76-8)

Guidance literature:

With oxygen; rose bengal; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -80 ℃; for 2h; Irradiation;

DOI:10.1016/S0040-4020(01)85353-9

Reference yield: 34.0%

(E)-2-[3-Hydroxy-3-[5-oxo-2-(2-trimethylsilanyl-ethoxy)-2,5-dihydro-furan-3-yl]-prop-(E)-ylidene]-6-methyl-8-(trimethyl-cyclohex-1-enyl)-oct-5-enal (214421-61-1) → seco-manoalide (105498-76-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1055/s-1998-6105

Reference yield:

Methyl (E)-3-methyl-5-(2,6,6-trimethylcyclohexen-1-yl)-2-pentenoate (4179-00-4) → seco-manoalide (105498-76-8)

Guidance literature:

Multi-step reaction with 11 steps

1: lithium aluminium hydride

2: PBr₃ / pyridine

4: 2N HCl / 0.05 h / 0 °C

6: 95 percent / diisobutylaluminium hydride / CH₂Cl₂

7: DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: LiCl / dimethylformamide / 0.5 h / 0 °C

10: O₂, rose bengal / CH₂Cl₂; methanol / -78 °C / Irradiation

11: 2N hydrochloric acid / tetrahydrofuran / 2 h / Ambient temperature

With hydrogenchloride; dmap; lithium aluminium tetrahydride; oxygen; phosphorus tribromide; rose bengal; diisobutylaluminium hydride; triethylamine; lithium chloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98937-8

upstream raw materials:

(E)-neomanoalide

(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

4-[(3Z,7E)-4-Dimethoxymethyl-1-(1-ethoxy-ethoxy)-8-methyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,7-dienyl]-5-hydroxy-5H-furan-2-one

4-[(3Z,7E)-4-Dimethoxymethyl-1-(1-ethoxy-ethoxy)-8-methyl-10-(2,6,6-trimethyl-cyclohex-1-enyl)-deca-3,7-dienyl]-5-hydroxy-5H-furan-2-one

Downstream raw materials:

5-Hydroxy-4-{6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethyl-cyclohex-1-enyl)-hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl}-5H-furan-2-one

manoalide

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

(+)-(R)-manoalide

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