(2R,3R)-3-Hydroxy-2-tetradecyloctadecanoic acid methyl ester

Base Information

• Chemical Name: (2R,3R)-3-Hydroxy-2-tetradecyloctadecanoic acid methyl ester
• CAS No.: 18951-36-5
• Molecular Formula: C₃₃H₆₆O₃
• Molecular Weight: 510.885
• Mol file: 18951-36-5.mol

Synonyms:(2R,3R)-3-Hydroxy-2-tetradecyl-octadecanoic acid methyl ester;methyl (2R,3R)-3-hydroxy-2-tetradecylocradecanoate;(2S,3R)-3-Hydroxy-2-tetradecyl-octadecansaeure-methylester (15D-Methoxycarbonyl-16D-hydroxy-hentriacontan);(2R,3R)-3-Hydroxy-2-tetradecyl-octadecansaeure-methylester;D-erythro-3-Hydroxy-2-tetradecyl-octadecansaeure-methylester;D-erythro-3-hydroxy-2-tetradecyl-octadecanoic acid methyl ester;

Chemical Property of (2R,3R)-3-Hydroxy-2-tetradecyloctadecanoic acid methyl ester

Chemical Property:

• PSA: 46.53000
• LogP: 10.70900

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2R,3R)-3-Hydroxy-2-tetradecyloctadecanoic acid methyl ester

There total 4 articles about (2R,3R)-3-Hydroxy-2-tetradecyloctadecanoic acid methyl ester 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: 32.0%

methyl α-palmitoyl palmitate (60715-65-3) → methyl (2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoate (87333-63-9) + methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate (17369-87-8,18951-36-5,23053-16-9,81872-27-7,87333-63-9,118204-68-5)

Guidance literature:

With sodium tetrahydroborate; In methanol; chloroform; for 4h; Ambient temperature;

DOI:10.1016/0008-6215(91)84089-W

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 5-hydroxy-2-methyl-4-tetradecyl-2-(trimethylsilyl)oxy-3-eicosanone (87280-55-5,87280-56-6) → methyl (2RS,3SR)-3-hydroxy-2-tetradecyloctadecanoate (87333-63-9) + methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate (17369-87-8,18951-36-5,23053-16-9,81872-27-7,87333-63-9,118204-68-5) + hexadecanoic acid methyl ester (112-39-0)

Guidance literature:

With periodic acid; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, room temp., 5 h, 2.) ether, 0 deg C;

DOI:10.1021/jo00171a035

Reference yield:

hexadecanoic acid methyl ester (112-39-0) → methyl (2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoate (17369-87-8,18951-36-5,23053-16-9,81872-27-7,87333-63-9,118204-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98.5 percent / xylene / 5 h / 145 °C

2: 32 percent / NaBH₄ / CHCl₃; methanol / 4 h / Ambient temperature

With sodium tetrahydroborate; In methanol; chloroform; xylene;

DOI:10.1016/0008-6215(91)84089-W

upstream raw materials:

diazomethane

(2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoic acid

5-hydroxy-2-methyl-4-tetradecyl-2-(trimethylsilyl)oxy-3-eicosanone

methyl α-palmitoyl palmitate

Downstream raw materials:

(2R,3R)-3-hydroxy-2-tetradecyloctadecanoic acid

dibenzyl ether

(2RS,3RS)-3-hydroxy-2-tetradecyloctadecanoic acid