LacCer(d18:1/16:0)

Base Information

• Chemical Name: LacCer(d18:1/16:0)
• CAS No.: 4201-62-1
• Molecular Formula: C₄₆H₈₇NO₁₃
• Molecular Weight: 862.196
• Nikkaji Number: J187.534E
• Wikidata: Q27158044
• Mol file: 4201-62-1.mol

Synonyms:4201-62-1;LacCer(d18:1/16:0);N-[(E,2S,3R)-1-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3-hydroxyoctadec-4-en-2-yl]hexadecanamide;beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-N-hexadecanoylsphingosine;N-[(1S,2R,3E)-1-[(4-O-beta-D-Galactopyranosyl-beta-D-glucopyranosyl)oxymethyl]-2-hydroxy-3-heptadecenyl]hexadecanamide;Cytopylin H;C16 Lactosylceramide (d18:1/16:0));SCHEMBL9362810;CHEBI:84758;Lactosyl ceramide (d18:1/16:0);AKOS040754843;C16 Lactosylceramide (d18:1/16:0);C16 Lactosyl Ceramide (d18:1/16:0);Q27158044;Hexadecanamide, N-[(1S,2R,3E)-1-[[(4-O-beta-D-galactopyranosyl-beta-D-glucopyranosyl)oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-;Hexadecanamide,N-[(1S,2R,3E)-1-[[(4-O-beta-D-galactopyranosyl-beta-D-glucopyranosyl)oxy]methyl]-2-hydroxy-3-heptadecen-1-yl]-;N-[(2S,3R,4E)-1-{[4-O-(beta-D-galactopyranosyl)-beta-D-glucopyranosyl]oxy}-3-hydroxyoctadec-4-en-2-yl]hexadecanamide

Chemical Property of LacCer(d18:1/16:0)

Chemical Property:

• XLogP3: 9.1
• Hydrogen Bond Donor Count: 9
• Hydrogen Bond Acceptor Count: 13
• Rotatable Bond Count: 36
• Exact Mass: 861.61774183
• Heavy Atom Count: 60
• Complexity: 1070

Purity/Quality:

C16 Lactosylceramide (d18:1/16:0) ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)O)O)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[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O)O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O

Technology Process of LacCer(d18:1/16:0)

There total 8 articles about LacCer(d18:1/16:0) 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: 76.2%

(2S,3R,4E)-[2',3',6'-tri-O-benzoyl-4'-O-(2'',3'',4'',6''-tetra-O-benzoyl-β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-3-O-benzoyl-4-octadecene-1,3-diol (167871-75-2) → (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-63-2,4889-49-0,7084-64-2,7228-69-5,16776-95-7,80124-66-9,150025-81-3,4201-62-1)

Guidance literature:

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

DOI:10.1080/07328300600859825

Reference yield:

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-58-5,4201-59-6,24696-34-2,52019-77-9,74743-19-4,102917-79-3,24696-26-2) + 4-O-(2,3,4,6-tetra-O-4-methoxybenzyl-β-D-galactopyranosyl)-2,3,6-tri-O-4-methoxybenzyl-D-glucopyranose + Methanesulfonic anhydride (7143-01-3) → (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-63-2,4889-49-0,7084-64-2,7228-69-5,16776-95-7,80124-66-9,150025-81-3,4201-62-1)

Guidance literature:

4-O-(2,3,4,6-tetra-O-4-methoxybenzyl-β-D-galactopyranosyl)-2,3,6-tri-O-4-methoxybenzyl-D-glucopyranose; With 1,2,2,6,6-pentamethylpiperidine; In dichloromethane; Inert atmosphere;

Methanesulfonic anhydride; In dichloromethane; at 23 ℃; for 0.166667h; Inert atmosphere;

(2S,3R,4E)-2-(hexadecanoylamido)-4-octadecene-1,3-diol; Further stages;

DOI:10.1039/c7cc01673e

Reference yield:

2-azido-sphingosine (103348-49-8) → (2S,3R,4E)-[4'-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl]-(1'->1)-2-(hexadecanoylamido)-4-octadecene-1,3-diol (4201-63-2,4889-49-0,7084-64-2,7228-69-5,16776-95-7,80124-66-9,150025-81-3,4201-62-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / pyridine; CHCl₃; tetrahydrofuran / 48 h / Ambient temperature

2: 91 percent / pyridine; toluene / 12 h / Ambient temperature

3: 90 percent / BF₃*OEt₂ / methanol; toluene / 5 h / Ambient temperature

4: BF₃*OEt₂ / CH₂Cl₂ / Ambient temperature

With boron trifluoride diethyl etherate; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; toluene;

upstream raw materials:

n-hexadecanoyl chloride

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

2-azido-sphingosine

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

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