Tetrahydrofuran → HCID 54244290, Verbindung

HRID 985986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 985986
C(OC([NH:11][C@H:12]([C@H:15]([C@@H:17]([C@@H:19]([CH2:21][OH:22])[OH:20])[OH:18])[OH:16])[CH:13]=O)=O)C1C=CC=CC=1.[CH2:23]([NH2:37])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[O:38]1[CH2:42][CH2:41][CH2:40][CH2:39]1>CN(C)C=O>[CH2:23]([N:37]([CH:13]1[O:20][C@H:19]([CH2:21][OH:22])[C@@H:17]([OH:18])[C@H:15]([OH:16])[C@H:12]1[NH2:11])[C:39](=[O:38])[CH2:40][CH2:41][CH2:42][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH3:23])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 16217TetradecylamineHCID 228512932-{[(Benzyloxy)carbonyl]amino}-2-deoxy-D-glucose

Produkt 1

HCID 54244290HCID 54244290, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3.1 g of 2-(benzyloxycarbonylamino)-2-deoxy-D-glucose were dissolved in 40 ml of dimethylformamide, 3.2 g of tetradecylamine were added and the mixture was warmed at 80° C. for 4 hours, under a water pump vacuum. The mixture was cooled to room temperature, diluted with 50 ml of tetrahydrofuran and stirred in the presence of 5 ml of ion exchanger SC 108 (H+ form). The exchanger resin was filtered off and 1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate. After the mixture had been stirred for five hours, the solid constituents were filtered off and the filtrate was evaporated in vacuo. The resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1).

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationThe exchanger resin was filtered off
  3. addition1 g of sodium carbonate and 3.3 g of stearoyl chloride were added to the filtrate
  4. filtrationthe solid constituents were filtered off
  5. customthe filtrate was evaporated in vacuo
  6. customThe resulting syrup was purified by column chromatography on silica gel (eluting agent methylene chloride/methanol=20:1)

Quellen und Nachweise

ORD-Eintrag
ord-bcc17d8ce8cc4242bd3995bd095814ab
Quelldatensatz
uspto-grants-1987_12
Patentnummer
US04710491

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