Triethylamine → HCID 86624083, Verbindung

HRID 2421811Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2421811
Cl.[OH:2][CH:3]1[O:11][C@H:10]([CH2:12][OH:13])[C@@H:8]([OH:9])[C@H:6]([OH:7])[C@@H:4]1[NH2:5].C(N([CH2:19][CH3:20])CC)C>CN(C=O)C>[C:3]([NH:5][C@H:4]1[C@@H:6]([OH:7])[C@H:8]([OH:9])[C@@H:10]([CH2:12][OH:13])[O:11][CH:3]1[OH:2])(=[O:2])[CH2:4][CH2:6][C:19]#[CH:20]

Komponenten

4

Edukt 2

HCID 8471TriethylamineHCID 9964480(3S,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol hydrochloride

Produkt 1

HCID 86624083HCID 86624083, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of D-mannosamine hydrochloride (863 mg, 4.0 mmol), N-succinimidyl 4-pentynoate 9 (781 mg, 4.0 mmol), triethylamine (1.67 ml, 12.0 mmol) in DMF (31 ml) was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, and the residue was purified by flash column chromatography (CHCl3/MeOH 8:1) to give N-4-Pentynoylmannosamine, 10 (898 mg, 87%); 1H-NMR (500 MHz, D2O) 2.37 (t, 2.63H, J=2.5 Hz), 2.48-2.63 (m, 10.5H), 3.38-3.42 (m, 1H), 3.52 (t, 1H, J=10 Hz), 3.63 (t, 1.63H, J=10 Hz), 3.69-3.91 (m, 7.89H), 4.05 (dd, 1.63H, J=4.5 and 10 Hz), 4.35 (dd, 1.63H, J=1.5 and 4.5 Hz), 4.47 (dd, 1H, J=1.5 and 4.5 Hz), 5.03 (d, 1H, J=1.5 Hz), 5.13 (d, 1.63H, J=1.5 Hz); 13C-NMR (125 MHz, D2O)□ 14.78, 14.91, 34.62, 34.79, 53.67, 54.50, 60.91, 60.93, 67.01, 67.28, 69.25, 70.56, 70.71, 72.47, 72.50, 76.80, 84.04, 84.45, 93.36, 93.67, 175.68, 176.41; ESI-TOF-HRMS m/e calculated for (M+H)+ C11H17NO6260.1129; found 260.1120.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash column chromatography (CHCl3/MeOH 8:1)

Quellen und Nachweise

ORD-Eintrag
ord-df0405d90c0d4f299deef28b841231e7
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960139B2

Notizen zur Reaktion

Wird geladen…