L-erythro-Sphingosine

Base Information

• Chemical Name: L-erythro-Sphingosine
• CAS No.: 6036-75-5
• Molecular Formula: C18H37NO2
• Molecular Weight: 299.49
• UNII: IZ0B386GUJ
• DSSTox Substance ID: DTXSID001319026
• Nikkaji Number: J259.750K,J2.324.266D
• Wikidata: Q27104581
• Metabolomics Workbench ID: 56740
• Mol file: 6036-75-5.mol

Synonyms:L-erythro-Sphingosine;6036-75-5;Erythro-sphingosine, (+)-;L-Erythro-c18-sphingosine;UNII-IZ0B386GUJ;IZ0B386GUJ;4-Octadecene-1,3-diol, 2-amino-, (2R,3S,4E)-;4-Octadecene-1,3-diol, 2-amino-, (S-(R*,S*-(E)))-;(2R,3S)-2-aminooctadec-4-ene-1,3-diol;(2R,3S,E)-2-aminooctadec-4-ene-1,3-diol;(2R,3S,4E)-2-aminooctadec-4-ene-1,3-diol;rel-(2R,3S,4E)-2-Amino-4-octadecene-1,3-diol;L-erythro-sphing-4-enine;(+)-erythro-sphingosine;(E,2R,3S)-2-aminooctadec-4-ene-1,3-diol;SCHEMBL17083789;CHEBI:46965;CHEBI:46967;L-erythro Sphingosine (d18:1);L-erythro-Sphingosine (synthetic);DTXSID001319026;AKOS040745780;(2R,3S)-2-Amino-4-octadecene-1,3-diol;Q27104581

Chemical Property of L-erythro-Sphingosine

Chemical Property:

• Vapor Pressure: 7.96E-10mmHg at 25°C
• Refractive Index: 1.489
• Boiling Point: 445.9 °C at 760 mmHg
• Flash Point: 223.5 °C
• PSA: 66.48000
• Density: 0.939 g/cm³
• LogP: 4.62450
• Storage Temp.: −20°C
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 15
• Exact Mass: 299.282429423
• Heavy Atom Count: 21
• Complexity: 231

Purity/Quality:

98% ^*data from raw suppliers

L-erythro Sphingosine (d18:1) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(CO)N)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@@H]([C@@H](CO)N)O

Technology Process of L-erythro-Sphingosine

There total 44 articles about L-erythro-Sphingosine 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%

(+/-)--4-(1-hydroxy-2-hexadecenyl)-2-oxazolidinone (86120-45-8,86120-49-2,89164-19-2,91109-04-5,91109-06-7,105308-75-6) → erythro-(E)-2-amino-4-octadecene-1,3-diol (123-78-4,871-45-4,2304-77-0,2733-29-1,6036-75-5,6036-85-7,10140-30-4,17673-73-3,25695-95-8,26308-91-8,88494-42-2,88494-43-3,89164-20-5)

Guidance literature:

With potassium hydroxide; ethanol; water; at 2.5 ℃; Reflux; Inert atmosphere;

DOI:10.1055/s-0028-1083367

Reference yield: 89.0%

rac-N-phthaloylsphingosine (109789-11-9) → erythro-(E)-2-amino-4-octadecene-1,3-diol (123-78-4,871-45-4,2304-77-0,2733-29-1,6036-75-5,6036-85-7,10140-30-4,17673-73-3,25695-95-8,26308-91-8,88494-42-2,88494-43-3,89164-20-5)

Guidance literature:

With hydrazine hydrate; In ethanol; for 1.5h; Heating;

Reference yield: 71.0%

(E)-1-(2-oxo-oxazolidin-4-yl)hexadec-2-en-1-yl pivalate → erythro-(E)-2-amino-4-octadecene-1,3-diol (123-78-4,871-45-4,2304-77-0,2733-29-1,6036-75-5,6036-85-7,10140-30-4,17673-73-3,25695-95-8,26308-91-8,88494-42-2,88494-43-3,89164-20-5)

Guidance literature:

With barium hydroxide octahydrate; In 1,4-dioxane; water; at 100 ℃; for 5h; Inert atmosphere;

DOI:10.1039/c4cc01312c

upstream raw materials:

(+/-)-threo-2-amino-octadec-4-yne-1,3-diol

1,1-diethoxy-hexadec-2-yne

2-nitro-4-octadecine-1,3-diol

2-Hexadecynal

Downstream raw materials:

(2S,3R,4E)-2-amino-4-octadecene-1,3-diol

dl-threo-triacetylsphingosine

dl-erythro-triacetylsphingosine

DL-threo-1-(Triphenylmethoxy)-2-myristoylamino-3-hydroxy-trans-octadecen-⁽⁴⁾

Refernces

• 1、 Guasch, Joan,Díaz, Yolanda,Matheu, M. Isabel,Castillón, Sergio. "Rhodium-catalyzed regio- and stereoselective oxyamination of dienes via tandem aziridination/ring-opening of dienyl carbamates". supporting information. p. 7344 - 7347. Retrieved 2014/07/07.
• 2、 Morales-Serna, Jose Antonio,Isabel Matheu, Yolanda Diaz M.,Castillon, Sergio. "Synthesis of D/L-erythro-Sphingosine Using a Tethered Aminohydroxylation Reaction as the Key Step". experimental part. p. 710 - 712. Retrieved 2009/09/06.