Methyl (2S)-2-hydroxyhexadecanoate

Base Information

• Chemical Name: Methyl (2S)-2-hydroxyhexadecanoate
• CAS No.: 78330-57-1
• Molecular Formula: C17H34O3
• Molecular Weight: 286.455
• DSSTox Substance ID: DTXSID40505701
• Nikkaji Number: J56.452D
• Wikidata: Q82360984
• Mol file: 78330-57-1.mol

Synonyms:Methyl (2S)-2-hydroxyhexadecanoate;78330-57-1;DTXSID40505701

Chemical Property of Methyl (2S)-2-hydroxyhexadecanoate

Chemical Property:

• XLogP3: 6.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 286.25079494
• Heavy Atom Count: 20
• Complexity: 216

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCC(C(=O)OC)O
• Isomeric SMILES: CCCCCCCCCCCCCC[C@@H](C(=O)OC)O

Technology Process of Methyl (2S)-2-hydroxyhexadecanoate

There total 38 articles about Methyl (2S)-2-hydroxyhexadecanoate 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%

methyl 2-oxo-hexadecanoate (55836-30-1) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5)

Guidance literature:

With formic acid; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; 3,3'-[(1R,2R)-1-amino-2-(4-dodecylphenylsulfonamido)ethane-1,2-diyl]bis(N,N,N-trimethylbenzenaminium)diiodide; sodium formate; In water; at 25 ℃; for 6h; enantioselective reaction;

DOI:10.1021/acs.joc.5b00241

Reference yield: 78.0%

methanol (67-56-1) + 1-O-β-D-glucopyranosyl-(2S,3R,5E,12E)-2N-[(2R)-hydroxyhexadecanoyl]-octadecasphinga-5,12-dienine (1356390-80-1) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5) + 1-O-β-D-glucopyranosylsphingosine (1356390-82-3)

Guidance literature:

With hydrogenchloride; at 60 ℃; for 15h;

Reference yield: 70.0%

1-iodotridecane (35599-77-0) + methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3) → methyl (R)-2-hydroxyhexadecanoate (16742-51-1,78330-57-1,89301-98-4,36451-47-5)

Guidance literature:

1-iodotridecane; With tert.-butyl lithium; In diethyl ether; pentane; at -78 - 20 ℃; Inert atmosphere;

With copper(I) bromide dimethylsulfide complex; dimethylsulfide; In diethyl ether; pentane; at 0 ℃; for 1h; Inert atmosphere;

methyl (2R)-glycidate; In diethyl ether; pentane; at -78 - -60 ℃; Inert atmosphere;

DOI:10.1039/b920285d

upstream raw materials:

methanol

(R)-(-)-2-hydroxyhexadecanoic acid

dimethyl sulfate

diazomethane

Downstream raw materials:

(2R)-(+)-1,2-hexadecanediol

(R)-(-)-2-hydroxyhexadecanoic acid

(S)-2-hydroxyhexadecanoic acid

methyl 2-oxo-hexadecanoate