Reaktion #2122478

Reaktionsgleichung

sphingosine

→

2b

C6-Ceramide

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONWhen completely in solution this mixture was added drop-wise
2. 2
   SonstigeThe reaction mixture was sealed
3. 3
   workup.WAITleft under N2 for two hours
4. 4
   SonstigeThe excess solvent was removed under pressure
5. 5
   SonstigeThis reaction procedure
6. 6
   SonstigeThe polarized light microscopy results
7. 7
   workup.ADDITIONwere simply mixed together
8. 8
   workup.WAITleft at room temperature
9. 9
   Sonstigeto evaporate

Vorschrift

2a (0.1 g(acid)) was dissolved in dichloromethane (3 mL) at room temperature under an atmosphere of nitrogen. A model compound from sphingosine derivatives (Ceramide (C2:0), (C4:0), (C6:0), (C8:0), (C10:0), (C12:0), (C14:0), (C16:0), (C17:0), (C18:0), (C18:1), (C20:0), (C24:0), (C24:1)) (0.1 g) was dissolved in dichloromethane (3 mL). When completely in solution this mixture was added drop-wise, over 15 minutes, to the oligofluoro (2a) in solution. The reaction mixture was sealed and left under N2 for two hours. The excess solvent was removed under pressure to allow the formation of the final product. The release/dissociation of the sphingosine compound (ceramide family) was confirmed using HPLC (0.5 mg/mL, injected 6 times, retention time 14.062 minutes) (FIG. 2l). This reaction procedure was further analyzed by polarized light microscopy and scanning electron microscopy. The polarized light microscopy results indicated that when the two components were simply mixed together and left at room temperature to allow the solvent to evaporate, a heterogenous matrix was formed (FIGS. 2a, 2b, 2c and 2d). This was further confirmed by scanning electron microscopy (FIGS. 2e, 2f, 2g and 2h). The homogeneity of the sample was further examined by using stainless steel unpolished metallic platforms. These platforms were coated with the product as a thin layer and then examined using scanning electron microscopy (FIGS. 2i and 2j). The results were indicative of a homogenous coating. Furthermore, the reaction procedure was analyzed to confirm that during the reaction and isolation of the final product the overall structure of the active compound was unaltered. Differential scanning electron microscopy (FIG. 2k) and NMR analysis confirmed the primary structure of the active compound remained intact. This composition was used to coat prototype devices which relates to endo-vascular devices. No phase separation was observed using Scanning Electron Microscopy (SEM) (FIGS. 2n, 2m, 2o and 2p).

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