7-E,9-E methyl trisporate B

Base Information

• Chemical Name: 7-E,9-E methyl trisporate B
• CAS No.: 31925-25-4
• Molecular Formula: C₁₉H₂₆O₄
• Molecular Weight: 318.413
• Mol file: 31925-25-4.mol

Synonyms:7-E,9-E methyl trisporate B

Chemical Property of 7-E,9-E methyl trisporate B

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7-E,9-E methyl trisporate B

There total 39 articles about 7-E,9-E methyl trisporate B 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: 93.0%

1,3-Dimethyl-2-[(1E,3E)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-4-oxo-cyclohex-2-enecarboxylic acid methyl ester (88661-73-8) → 7-E,9-E methyl trisporate B (31925-25-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 5h;

DOI:10.1021/jo00225a049

Reference yield:

4-penten-3-one (1629-58-9) → 7-E,9-E methyl trisporate B (31925-25-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / triethylamine / tetrahydrofuran / 6 h / Heating

2: 95 percent / p-toluenesulfonic acid / benzene / 36 h / Heating

3: 100 percent / N-bromosuccinimide, benzoyl peroxide / CCl₄ / 3 h / Heating

4: 89 percent / water / 0.08 h / 100 °C

5: 1.) n-butyllithium, 2.) hexamethylphosphoramide / 1.) THF, hexane, 10 min, 2.) THF, hexane, -78 deg C to 0 deg C, 2.5 h

6: diethyl ether

7: 93 percent / 5percent hydrochloric acid / tetrahydrofuran / 5 h / 0 °C

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; N-Bromosuccinimide; n-butyllithium; Perbenzoic acid; water; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; tetrachloromethane; diethyl ether; benzene;

DOI:10.1021/jo00225a049

Reference yield:

1,3-Dimethyl-2-[(1E,3E)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-4-oxo-cyclohex-2-enecarboxylic acid methyl ester → 7-E,9-Z methyl trisporate B (69854-98-4) + 7-E,9-E methyl trisporate B (31925-25-4)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 0 ℃; for 5.5h; Yield given. Yields of byproduct given;

DOI:10.1021/jo00225a049

upstream raw materials:

Methyl 1,3-Dimethyl-2-formyl-4-oxocyclohex-2-enyl-1-carboxylat

<(E)-6,6-(ethylenedioxy)-2-methyl-2-heptenyl>triphenylphosphonium bromide

(4E,6E)-2,6-Dimethyl-3,10-dioxo-2-(3-oxo-pentyl)-undeca-4,6-dienoic acid methyl ester

(4E,6Z)-2,6-Dimethyl-3,10-dioxo-2-(3-oxo-pentyl)-undeca-4,6-dienoic acid methyl ester

Refernces

• 1、 Trost, Barry M.,Ornstein, Paul L.. "BIFUNCTIONAL CYCLOPROPYL REAGENTS: A TOTAL SYNTHESIS OF 7-E,9-Z METHYL TRISPORATE B". . p. 2833 - 2836. Retrieved 2007/10/02.