Triethylamine → HCID 178434963, Verbindung

HRID 964701

Reaktionsgleichung

Reaktionsgleichung von HRID 964701
C(N(CC)CC)C.[CH:8]1([O:18][P:19]([O-:22])([O-:21])=[O:20])[O:16][C@@H:15]([CH3:17])[C@@H:13]([OH:14])[C@@H:11]([OH:12])[C@@H:9]1[OH:10].C([NH+](CC)CC)C.C([NH+](CC)CC)C.C1CCC(NC(N2CCOCC2)=NC2CCCCC2)CC1.C1N([P:64]([O:67][CH2:68][C@H:69]2[O:73][C@@H:72]([N:74]3[C:78]4[NH:79][C:80]([NH2:84])=[N:81][C:82](=[O:83])[C:77]=4[N:76]=[CH:75]3)[C@H:71]([OH:85])[C@@H:70]2[OH:86])([OH:66])=[O:65])CCOC1.N1C=NN=N1>N1C=CC=CC=1>[CH3:17][CH:15]1[O:16][CH:8]([O:18][P:19]([O:21][P:64]([O:67][CH2:68][CH:69]2[O:73][CH:72]([N:74]3[C:78]4[NH:79][C:80]([NH2:84])=[N:81][C:82](=[O:83])[C:77]=4[N:76]=[CH:75]3)[CH:71]([OH:85])[CH:70]2[OH:86])([OH:66])=[O:65])([OH:22])=[O:20])[CH:9]([OH:10])[CH:11]([OH:12])[CH:13]1[OH:14]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 67630241Triethylammonium fucosyl phosphateHCID 178418441HCID 178418441, VerbindungHCID 178420494HCID 178420494, Verbindung

Produkt 1

HCID 178434963HCID 178434963, VerbindungAusbeute 87,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel2×

Versuchsvorschrift

Compound 26 (624 mg, 1.41 mmol; wherein R, R'=OH; Sigma) was dissolved in H2O (15 mL), applied to a Bio-Rad AG 50W-X2 cation exchange column (Et3N+, 2.5×8 cm), and eluted with H2O (150 mL). The solution was evaporated, coevaporated with MeOH (2×10 mL) and dried for 3 d under vacuum to give triethylammonium β-L-fucopyranosyl phosphate 29 (512 mg). The content of triethylamine was determined to be 1.16 equiv. (1H NMR) A mixture of 29 (57.5 mg, 159 μmol) and guanosine 5'-monophospho morpholidate 4-morpholine-N,N'-dicyclohexylcarboxamidine salt 27 (201 mg, 255 μmol) was coevaporated with dry pyridine (3×1.5 mL). 1H-Tetrazole (33 mg, 477 μmol) and dry pyridine (0.8 mL) were added, and the solution stirred at rt. After a while, product starts to precipitate. The reaction was monitored by TLC (2:1 i-PrOH/1M NH4OAc). After 2 d, the mixture was diluted with water (1.5 mL) to become a clear solution, evaporated, and coevaporated with water (2×1.5 mL). The residue was purified on a Bio-Gel P-2 column (2.5×70 cm), eluated with 250 mM NH4 HCO3 to give 30 (82.4 mg, 85%) as a white solid after lyophilization (Rf 0.43, 2:1 i-PrOH/1M NH4OAc). The 1H NMR spectral data were in agreement with the published ones (Nunez et al. Can. J. Chem. 1981, 59, 2086-2095; Gokhale et al. Can. J. Chem. 1990, 68, 1063-1071).

Aufarbeitung

  1. customto precipitate
  2. additionthe mixture was diluted with water (1.5 mL)
  3. customevaporated
  4. customThe residue was purified on a Bio-Gel P-2 column (2.5×70 cm)

Quellen und Nachweise

ORD-Eintrag
ord-decea63b13e2414e8448006e4c31bfb5
Quelldatensatz
uspto-grants-1998_06
Patentnummer
US05770407

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