Glucosylsphingosine

Base Information

• Chemical Name: Glucosylsphingosine
• CAS No.: 52050-17-6
• Molecular Formula: C24H47 N O7
• Molecular Weight: 461.63
• Hs Code.: 2932990090
• DSSTox Substance ID: DTXSID101315465
• Metabolomics Workbench ID: 65897
• Nikkaji Number: J675.987D
• Mol file: 52050-17-6.mol

Synonyms:GlcSph;glucopsychosine;glucosyl psychosine;glucosyl sphingosine;glucosylsphingosine;sphingosyl beta-glucoside

Chemical Property of Glucosylsphingosine

Chemical Property:

• Vapor Pressure: 1.77E-20mmHg at 25°C
• Boiling Point: 664.3°Cat760mmHg
• Flash Point: 355.6°C
• PSA: 145.63000
• Density: 1.14g/cm³
• LogP: 2.44870
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 461.33525284
• Heavy Atom Count: 32
• Complexity: 479

Purity/Quality:

97% ^*data from raw suppliers

Glucosyl-C18-sphingosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): 4333674
• Hazard Codes: B

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC=CC(C(COC1C(C(C(C(O1)CO)O)O)O)N)O
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)N)O
• Uses: Glucosyl(β) Sphingosine (d18:1) or D-glucosyl-β1-1′-D-erythro-sphingosine may be used: to screen lipids that rapidly and reversibly alter?transepithelial?electrical resistance (TER) or tight junction (TJ) permeability in epithelial tissue as a standard for the quantification of glucosyl sphingosine?in Gaucher patients using liquid chromatography electrospray ionization tandem mass spectrometric (LC/ESI-MS/MS) as an internal standard for the quantification of lysoglucosylceramide in plasma for Gaucher disease using liquid chromatography with tandem mass spectrometry (LC-MS/MS) A sphingosine derivative. A sphingolipid compound found in the the umbilical cord artery of women with preeclampsia.

Technology Process of Glucosylsphingosine

There total 34 articles about Glucosylsphingosine 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: 94.0%

Benzoic acid (E)-(R)-1-[(S)-1-azido-2-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl]-hexadec-2-enyl ester (172340-52-2) → Glucosylsphingosine (52050-17-6)

Guidance literature:

With hydrogen sulfide; In pyridine; water; for 24h; Ambient temperature;

Reference yield: 88.0%

(2S,3R,4E)-β-D-glucopyranosyl-(1'<->1)-2-azido-4-octadecene-1,3-diol (108283-60-9) → Glucosylsphingosine (52050-17-6)

Guidance literature:

With pyridine; hydrogen sulfide; In water; for 48h;

DOI:10.1016/S0009-3084(01)00152-9

Reference yield: 80.0%

(2S,3R,4E)-2-azido-1-(galactopyranosyloxy)octadec-4-en-3-ol (118711-45-8) → psychosine (2238-90-6,52050-17-6,56453-02-2,95119-84-9,95975-32-9,106565-70-2)

Guidance literature:

With pyridine; hydrogen sulfide; In water; for 48.25h;

upstream raw materials:

α-galactosyl fluoride

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

(2,3,4,6-tetra-O-pivaloyl-α-D-galactopyranoside)-1-trichloroacetimidate

(2S,3R,4E)-2-azido-1-(galactopyranosyloxy)octadec-4-en-3-ol

Downstream raw materials:

(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(octadecanoylamino)-3-hydroxyoctadec-4-ene

(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(15(Z)-tetracosenoylamino)-3-hydroxyoctadec-4-ene

(2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene

N-Acetylpsychosine