5-methyl-3-[(8R,11Z,19Z)-2,8,15,16-tetrahydroxytriaconta-11,19-dien-1-yl]furan-2(5H)-one

Base Information

• Chemical Name: 5-methyl-3-[(8R,11Z,19Z)-2,8,15,16-tetrahydroxytriaconta-11,19-dien-1-yl]furan-2(5H)-one
• CAS No.: 151484-76-3
• Molecular Formula: C₃₅H₆₄O₆
• Molecular Weight: 580.89
• Mol file: 151484-76-3.mol

Synonyms:2(5H)-Furanone,5-methyl-3-(2,8,15,16-tetrahydroxy-11-triacontenyl)-,[5S-[3(2S*,8S*,11Z,15S*,16S*),5R*]]-; 2(5H)-Furanone,5-methyl-3-[(2R,8R,11Z,15R,16R)-2,8,15,16-tetrahydroxy-11-triacontenyl]-, (5S)-(9CI); Giganin

Chemical Property of 5-methyl-3-[(8R,11Z,19Z)-2,8,15,16-tetrahydroxytriaconta-11,19-dien-1-yl]furan-2(5H)-one

Chemical Property:

• Vapor Pressure: 1.16E-24mmHg at 25°C
• Boiling Point: 730.9°C at 760 mmHg
• Flash Point: 218.4°C
• Density: 1.022g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-methyl-3-[(8R,11Z,19Z)-2,8,15,16-tetrahydroxytriaconta-11,19-dien-1-yl]furan-2(5H)-one

There total 17 articles about 5-methyl-3-[(8R,11Z,19Z)-2,8,15,16-tetrahydroxytriaconta-11,19-dien-1-yl]furan-2(5H)-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: 99.0%

(S)-3-((2R,8R,Z)-2,8-bis((tert-butyldimethylsilyl)oxy)-14-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)tetradec-11-en-1-yl)-5-methylfuran-2(5H)-one (1449472-14-3) → (+)-giganin (151484-76-3)

Guidance literature:

With acetyl chloride; In methanol; at 20 ℃; for 24h;

DOI:10.1002/anie.201208403

Reference yield:

1-Bromotetradecane (112-71-0) → (+)-giganin (151484-76-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: magnesium; iodine / diethyl ether / 2 h / 20 °C

1.2: 2 h / 0 - 20 °C

2.1: propionic acid / benzene / 2 h / 150 °C

3.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 19 h / 0 °C

4.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux

5.1: toluene-4-sulfonic acid / toluene / 60 °C

6.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

7.2: -78 - 20 °C

8.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / tert-butyl methyl ether / 5 h / -78 °C

8.2: 21 h / -78 °C / Reflux

9.1: 1H-imidazole / dichloromethane / 20 °C

10.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 - 0 °C

10.2: 3 h / 20 °C

11.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 0 °C

12.1: acetyl chloride / methanol / 24 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; magnesium; propionic acid; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; water; toluene; tert-butyl alcohol; benzene; 2.1: |Johnson-Claisen Rearrangement / 7.1: |Wittig Olefination / 7.2: |Wittig Olefination;

DOI:10.1002/anie.201208403

Reference yield:

(E)-ethyl nonadec-4-enoate (909270-38-8) → (+)-giganin (151484-76-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: methanesulfonamide; AD-mix β / tert-butyl alcohol; water / 19 h / 0 °C

2.1: lithium aluminium tetrahydride / diethyl ether / 2 h / 0 °C / Reflux

3.1: toluene-4-sulfonic acid / toluene / 60 °C

4.1: 1H-imidazole; iodine / dichloromethane / 2.5 h / 0 - 20 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 0 - 20 °C

5.2: -78 - 20 °C

6.1: sec.-butyllithium; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine / tert-butyl methyl ether / 5 h / -78 °C

6.2: 21 h / -78 °C / Reflux

7.1: 1H-imidazole / dichloromethane / 20 °C

8.1: lithium diisopropyl amide / tetrahydrofuran / 0.75 h / -78 - 0 °C

8.2: 3 h / 20 °C

9.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.25 h / 0 °C

10.1: acetyl chloride / methanol / 24 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; methanesulfonamide; AD-mix β; iodine; sec.-butyllithium; sodium hexamethyldisilazane; toluene-4-sulfonic acid; acetyl chloride; 3-chloro-benzenecarboperoxoic acid; (1R,5S,11aS)-3-methyldecahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; tert-butyl methyl ether; water; toluene; tert-butyl alcohol; 5.1: |Wittig Olefination / 5.2: |Wittig Olefination;

DOI:10.1002/anie.201208403

upstream raw materials:

1-Bromotetradecane

(E)-ethyl nonadec-4-enoate

(R)-5-((R)-1-hydroxypentadecyl)-dihydrofuran-2(3H)-one

3-((4R,5R)-2,2-dimethyl-5-tetradecyl-1,3-dioxolan-4-yl)propan-1-ol

Downstream raw materials:

gigantetrocin A

goniothalamicin

Refernces