N-(hexadecanoyl)-beta-D-galactosylsphingosine

Base Information

• Chemical Name: N-(hexadecanoyl)-beta-D-galactosylsphingosine
• CAS No.: 34324-89-5
• Molecular Formula: C40H77NO8
• Molecular Weight: 700.0413
• DSSTox Substance ID: DTXSID901120367
• Nikkaji Number: J502.164B,J775.351I
• Wikidata: Q27105092
• Mol file: 34324-89-5.mol

Synonyms:C16-GalCer;N-palmitoyl galactosyl-C18-sphingosine;N-palmitoylgalactosylsphingosine;N-palmitoylpsychosine;NPGS;NPoGS

Chemical Property of N-(hexadecanoyl)-beta-D-galactosylsphingosine

Chemical Property:

• Vapor Pressure: 5.17E-33mmHg at 25°C
• Boiling Point: 842.8°Cat760mmHg
• PKA: 12.92±0.70(Predicted)
• Flash Point: 463.5°C
• PSA: 152.20000
• Density: 1.05g/cm³
• LogP: 8.22750
• Storage Temp.: ?20°C
• XLogP3: 11.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 33
• Exact Mass: 699.56491841
• Heavy Atom Count: 49
• Complexity: 783

Purity/Quality:

99% ^*data from raw suppliers

N-HEXADECANOYL CEREBROSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)O)O)O)C(C=CCCCCCCCCCCCCC)O
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O

Technology Process of N-(hexadecanoyl)-beta-D-galactosylsphingosine

There total 40 articles about N-(hexadecanoyl)-beta-D-galactosylsphingosine 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: 95.0%

(2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine (94069-99-5,94132-56-6,116558-60-2,124377-35-1) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene (34324-89-5)

Guidance literature:

With sodium methylate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1016/S0040-4039(00)86684-8

Reference yield: 85.0%

(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (183667-71-2) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene (34324-89-5)

Guidance literature:

With sodium methylate; In methanol; dichloromethane; at 20 ℃; for 12h; pH=9;

DOI:10.1080/07328300600859825

Reference yield: 80.0%

psychosine (2238-90-6,52050-17-6,56453-02-2,95119-84-9,95975-32-9,106565-70-2) + n-hexadecanoyl chloride (112-67-4) → (2S,3R,4E)-1-(β-D-galactopyranosyloxy)-2-(hexadecanoylamino)-3-hydroxyoctadec-4-ene (34324-89-5)

Guidance literature:

With sodium acetate; In tetrahydrofuran; water; at 20 ℃; for 3h;

DOI:10.1016/S0040-4020(02)01092-X

upstream raw materials:

(2S,3R)-N-palmitoyl-3-O-benzoyl-1-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-D-sphingosine

psychosine

n-hexadecanoyl chloride

(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

Downstream raw materials:

(2S,3R,4E)-2',3',4',6'-tetra-O-benzoyl-β-D-galactopyranosyl-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol

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