1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 6-(2',6'-Diaminohexanoylamino)-3,4,5-Trihydroxytetra-Hydropyran-2-ylmethyl 10,12-Tricosadiynoate

HRID 865619

Reaktionsgleichung

Reaktionsgleichung von HRID 865619
[NH2:1][C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].[NH:13](C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H:14]([C:27](OC1C(F)=C(F)C(F)=C(F)C=1F)=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][NH:19]C(OC(C)(C)C)=O.[C:58]([OH:82])(=O)[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67]#[C:68][C:69]#[C:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80].C(N=C=NCCCN(C)C)C>CN(C)C=O>[C:58]([O:12][CH2:11][CH:9]1[CH:7]([OH:8])[CH:5]([OH:6])[CH:3]([OH:4])[CH:2]([NH:1][C:27](=[O:28])[CH:14]([NH2:13])[CH2:15][CH2:16][CH2:17][CH2:18][NH2:19])[O:10]1)(=[O:82])[CH2:59][CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][C:67]#[C:68][C:69]#[C:70][CH2:71][CH2:72][CH2:73][CH2:74][CH2:75][CH2:76][CH2:77][CH2:78][CH2:79][CH3:80]

Komponenten

6

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 53845710,12-Tricosadiynoic AcidHCID 11095207(2R,3R,4S,5R,6R)-2-Amino-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triolHCID 11146634Fmoc-Lys(Boc)-OPfp

Produkt 1

HCID 186889666-(2',6'-Diaminohexanoylamino)-3,4,5-Trihydroxytetra-Hydropyran-2-ylmethyl 10,12-Tricosadiynoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1-Amino-1-deoxy-β-D-galactose (180 mg, 1 mmol), and Fmoc-Lys(Boc)-OPfp (650 mg, 1 mmol) were dissolved in 4 ml dry dimethylformamide and stirred at room temperature overnight. The solvent was removed in vacuo, the residue was redissolved in acetonitrile/water (1:1), filtered and purified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35). The relevant fractions were collected, concentrated in vacuo, and the product was characterised by NMR. The purified product (1 g, 1 mmol), 10,12-tricosadiynoic acid (350 mg, 1 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide are dissolved in 10 ml dry dimethylformamide and stirred at room temperature overnight. The solvent is removed in vacuo, the residue redissolved in chloroform/methanol (95:5), filtered and purified by straight phase chromatography on a CHROMATOTRON. The relevant fractions are collected, concentrated in vacuo, and the product is characterised by NMR. The protecting groups of the α-ε amino groups are removed by standard reactions. Boc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes. The solvent is removed in vacuo. Fmoc is removed by treating the residue with 20% piperidine in dimethylformamide for 30 minutes, and the solvent is removed in vacuo. The final product is purified by reversed phase chromatography (Lobar RPSB).

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was redissolved in acetonitrile/water (1:1)
  3. filtrationfiltered
  4. custompurified by reversed phase chromatography (Lobar RPSB, acetonitrile/water 50:50 and 65:35)
  5. customThe relevant fractions were collected
  6. concentrationconcentrated in vacuo
  7. stirringstirred at room temperature overnight
  8. customThe solvent is removed in vacuo
  9. dissolutionthe residue redissolved in chloroform/methanol (95:5)
  10. filtrationfiltered
  11. custompurified by straight phase chromatography on a CHROMATOTRON
  12. customThe relevant fractions are collected
  13. concentrationconcentrated in vacuo
  14. customThe protecting groups of the α-ε amino groups are removed by standard reactions
  15. customBoc is removed by treatment with trifluoroacetic acid/methylene chloride for 30 minutes
  16. customThe solvent is removed in vacuo
  17. customFmoc is removed
  18. additionby treating the residue with 20% piperidine in dimethylformamide for 30 minutes
  19. customthe solvent is removed in vacuo
  20. customThe final product is purified by reversed phase chromatography (Lobar RPSB)

Quellen und Nachweise

ORD-Eintrag
ord-88e0b7008bdd4509972906eebe10c0a0
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567413

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