(2R,3S,4S)-2-Undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid

Base Information

• Chemical Name: (2R,3S,4S)-2-Undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid
• CAS No.: 70579-56-5
• Molecular Formula: C17H30O4
• Molecular Weight: 298.41800
• Mol file: 70579-56-5.mol

Synonyms:(2R,3S,4S)-4-Methyl-5-oxo-2-undecyl-tetrahydro-furan-3-carboxylic acid;(+)-naphrosteranic acid;(2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acid;(2R,3S,4S)-4-methyl-5-oxo-2-undecyltetrahydrofuran-3-carboxylic acid;(+)-neophrosteranic acid;(2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid;

Chemical Property of (2R,3S,4S)-2-Undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid

Chemical Property:

• Melting Point: 97 °C
• Boiling Point: 457.8±38.0 °C(Predicted)
• PKA: 3.86±0.60(Predicted)
• PSA: 63.60000
• Density: 1.012±0.06 g/cm3(Predicted)
• LogP: 4.16960

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3S,4S)-2-Undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid

There total 46 articles about (2R,3S,4S)-2-Undecyl-4-methyl-5-oxotetrahydrofuran-3-carboxylic acid 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: 100.0%

(2R,3S)-(+)-2-undecyl-5-oxo-tetrahydrofuran-3-carboxylic acid (626201-54-5) + methyl iodide (74-88-4) → (2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acid (70579-56-5)

Guidance literature:

(2R,3S)-(+)-2-undecyl-5-oxo-tetrahydrofuran-3-carboxylic acid; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.5h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 2h;

DOI:10.1039/c6ob02398c

Reference yield: 89.0%

(3S,4S,5R)-3-Methyl-4--5-undecyl-4,5-dihydro-2(3H)-furanone (157497-28-4) → (2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acid (70579-56-5)

Guidance literature:

With boron trifluoride diethyl etherate; mercury(II) oxide; In tetrahydrofuran; water;

DOI:10.1016/S0040-4039(00)73129-7

Reference yield: 86.0%

4-(S)-methyl-5-oxo-2-(R)-undecyloxolane-3-(R)-carboxylic acid (405552-35-4) → (2R,3S,4S)-(+)-2-undecyl-4-methyl-5-oxo-tetrahydrofuran-3-carboxylic acid (70579-56-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In toluene; for 72h; Heating;

DOI:10.1139/cjc-79-11-1727

upstream raw materials:

(3S,4S,5R)-3-Methyl-4--5-undecyl-4,5-dihydro-2(3H)-furanone

4-(S)-methyl-5-oxo-2-(R)-undecyloxolane-3-(R)-carboxylic acid

(2R,3S)-(+)-2-undecyl-5-oxo-tetrahydrofuran-3-carboxylic acid

methyl iodide