(3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

Base Information

• Chemical Name: (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one
• CAS No.: 169895-26-5
• Molecular Formula: C₄₀H₅₄O₃
• Molecular Weight: 582.867
• Mol file: 169895-26-5.mol

Synonyms:

Chemical Property of (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

There total 12 articles about (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-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:

<1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate (70905-70-3) → (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one (169895-26-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 50 percent / Bu₄NReO₄, TsOH*2H₂O / CH₂Cl₂ / 10 h / Ambient temperature

2: 80 percent / 0.02percentI₂ / heptane / 0.8 h / Heating

3: aq. K₂CO₃ / methanol / 0.25 h / 0 °C

4: LiCl, MsCl, γ-collidine / dimethylformamide / 1.5 h / 0 °C

5: CHCl₃ / 19 h / Heating

6: 1.) NaOMe, 2.) aq. NaOH / 1.) CH₂Cl₂, 0 deg C, 2 h, 2.) MeOH, room temp., 15 min

7: 87 percent / PdCl₂(MeCN)2, Et₃N, H₂O / acetonitrile / 2.5 h / Ambient temperature

8: NaOMe / CH₂Cl₂; methanol / 0.25 h / 0 °C

With 2,4,6-trimethyl-pyridine; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; water; iodine; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; tetrabutylammonium perrhenate; lithium chloride; In methanol; n-heptane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

<1R,4R,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate (152187-03-6) → (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one (169895-26-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 58 percent / Bu₄NReO₄, TsOH*2H₂O / CH₂Cl₂ / 10 h / Ambient temperature

2: 80 percent / 0.02percentI₂ / heptane / 0.8 h / Heating

3: aq. K₂CO₃ / methanol / 0.25 h / 0 °C

4: LiCl, MsCl, γ-collidine / dimethylformamide / 1.5 h / 0 °C

5: CHCl₃ / 19 h / Heating

6: 1.) NaOMe, 2.) aq. NaOH / 1.) CH₂Cl₂, 0 deg C, 2 h, 2.) MeOH, room temp., 15 min

7: 87 percent / PdCl₂(MeCN)2, Et₃N, H₂O / acetonitrile / 2.5 h / Ambient temperature

8: NaOMe / CH₂Cl₂; methanol / 0.25 h / 0 °C

With 2,4,6-trimethyl-pyridine; dichloro bis(acetonitrile) palladium(II); sodium hydroxide; water; iodine; sodium methylate; potassium carbonate; toluene-4-sulfonic acid; methanesulfonyl chloride; triethylamine; tetrabutylammonium perrhenate; lithium chloride; In methanol; n-heptane; dichloromethane; chloroform; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial (5056-17-7) → (3E,5E,7E,9E,11E,13E,15E)-1,18-Bis-((R)-4-hydroxy-2,6,6-trimethyl-cyclohex-1-enyl)-3,7,12,16-tetramethyl-octadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one (169895-26-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NaOMe, 2.) aq. NaOH / 1.) CH₂Cl₂, 0 deg C, 2 h, 2.) MeOH, room temp., 15 min

2: 87 percent / PdCl₂(MeCN)2, Et₃N, H₂O / acetonitrile / 2.5 h / Ambient temperature

3: NaOMe / CH₂Cl₂; methanol / 0.25 h / 0 °C

With dichloro bis(acetonitrile) palladium(II); sodium hydroxide; water; sodium methylate; triethylamine; In methanol; dichloromethane; acetonitrile;

upstream raw materials:

(2E,4E,6E,8E,10E)-13-(4-hydroxy-2,6,6-trimethylcyclohex-1-enyl)-2,7,11-trimethyl-12-oxotrideca-2,4,6,8,10-pentaenal

(2E,4E,6E)-2,7-dimethyl-2,4,6-octatrienedial

<1R,4S,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

<1R,4R,5R-(E)>-4-(5-Acetoxy-3-methylpent-3-en-1-ynyl)-4-hydroxy-3,3,5-trimethylcyclohexyl acetate

Downstream raw materials:

halocyanthiaxanthin