1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol

Base Information

• Chemical Name: 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol
• CAS No.: 136770-76-8
• Molecular Formula: C19H41NO2
• Molecular Weight: 315.53
• DSSTox Substance ID: DTXSID90438358
• Nikkaji Number: J1.698.152D
• Wikidata: Q27147847
• Mol file: 136770-76-8.mol

Synonyms:1-O-hexadecyl-2-desoxy-2-amino-sn-glycerol;1-O-hexadecyl-2-desoxy-2-aminoglycerol

Chemical Property of 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol

Chemical Property:

• PSA: 55.48000
• LogP: 5.50420
• Storage Temp.: -15°C
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 18
• Exact Mass: 315.313729551
• Heavy Atom Count: 22
• Complexity: 200

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCCOCC(CO)N
• Isomeric SMILES: CCCCCCCCCCCCCCCCOC[C@H](CO)N
• Uses: 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol is a substrate for human sphingosine kinase.

Technology Process of 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol

There total 7 articles about 1-O-Hexadecyl-2-desoxy-2-amino-sn-glycerol 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%

(R)-4-(hexadecyloxymethyl)-3-oxazolidin-2-one (1353577-11-3) → 1-O-hexadecyl-2-amino-2-deoxy-sn-glycerol (136770-76-8,151312-95-7)

Guidance literature:

With lithium hydroxide monohydrate; In ethanol; for 1h; Reflux;

DOI:10.1016/j.tetasy.2011.11.002

Reference yield:

methanesulfonic acid hexadecyl ester (20779-14-0) → 1-O-hexadecyl-2-amino-2-deoxy-sn-glycerol (136770-76-8,151312-95-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / tetrahydrofuran / 20 - 50 °C

1.2: tetrahydrofuran / 12 h / Heating

2.1: BF₃; MeOH / 20 °C

With methanol; boron trifluoride; sodium hydride; In tetrahydrofuran; 1.1: deprotonation / 1.2: Etherification / 2.1: detritylation;

DOI:10.1016/S0009-3084(00)00156-0

Reference yield:

1-O-hexadecyl-2-N-trityl-2-amino-2-deoxy-3-O-trityl-sn-glycerol → 1-O-hexadecyl-2-amino-2-deoxy-sn-glycerol (136770-76-8,151312-95-7)

Guidance literature:

With methanol; boron trifluoride; at 20 ℃;

DOI:10.1016/S0009-3084(00)00156-0

upstream raw materials:

4-Hexadecyloxymethyl-2-phenyl-4,5-dihydro-oxazole

methanesulfonic acid hexadecyl ester

(4R,αS)-4-(hexadecyloxymethyl)-3-(α-methylbenzyl)oxazolidin-2-one

(R)-4-(hexadecyloxymethyl)-3-oxazolidin-2-one

Downstream raw materials:

(R)-3-hexadecyloxy-(3-(R)-α-methylbenzylureido)prop-2-yl acetate

(R)-3-hexadecyloxy-(3-(S)-α-methylbenzylureido)prop-2-yl acetate

Hexadecanoic acid ((S)-2-hexadecyloxy-1-hydroxymethyl-ethyl)-amide