Trifluoroacetic acid → 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose

HRID 2050670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2050670
[CH2:1]([O:8][C@H:9]1[C@H:15]2[CH2:16][CH2:17][NH:18][C@@H:10]1[C@@H:11]([O:14]2)[O:12]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)[C:21]([OH:23])=[O:22]>O>[CH2:1]([O:8][C@H:9]1[C@H:15]([OH:14])[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:22])[C@@H:10]1[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 14523439methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-beta-D-lyxo-hexofuranoside

Produkt 1

HCID 1317168873-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexoseAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-β-D-lyxo-hexofuranoside (23β) (762 mg, 2.06 mmol) in a 1:1 mixture of trifluoroacetic acid and water (20 ml) was stirred at room temperature for 20 minutes. The solvents were removed in vacuo and the crude material purified by flash chromatography (ethyl acetate-hexane 1:2) to give 3-O-benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose (640 mg, 87%) as a clear oil, [α]20D -17.2° (c, 0.73 in chloroform); νmax (film) 3400 (OH), 2920, 1690 (C=O), 1410, 1345 and 1060 cm-1 ; 1H NMR δ 1.50-1.71 (1H, m, H-5); 1.80 (1H, bs, OH); 2.02-2.20 (1H, m, H-5'); 3.08-3.27 (1H, m, H-6); 3.94-4.20 (2H, m, 6-H, H-3); 4.25-4.85 (4H, m, H-2, H-4, CH2 -Ph); 5.05-5.18 (2H, m, CH2 -Z); 5.50, 5.53 (0.75H, 2×s, H-1-hemiacetal); 7.20-7.40 (10H, m, 2×H-Ph); 9.68 (0.25H, s, H-1-aldehyde). 13C NMR δ 24.17 (t, C-5); 38.10 (t, C-6); 57.26, 57.77 (2×d, C-2); 67.30, 67.48, 67.58 (3×t, CH2 -Z); 71.38, 71.84, 72.12 (3×t, CH2Ph); 74.00, 74.63, 74.76 (3×d, C-3, C-4); 98.72, 98.88, 198.17 (3×d, C-1); 127.35, 127.58, 127.85, 128.01, 128.23, 128.63 (6×d, HC-Ph); 136.51, 136.62, 136.73, 137.46, 155.60 (s, C=O-Z); 137.74, 137.88 (6×s, C-Ph). m/z: 91 (100%), 262 (20%), 370 (M+H+, 15%). (Found C, 68.68; H, 6.40; N, 3.71. C21H23NO5 requires C, 68.28; H, 6.28; N, 3.79).

Aufarbeitung

  1. customThe solvents were removed in vacuo
  2. customthe crude material purified by flash chromatography (ethyl acetate-hexane 1:2)

Quellen und Nachweise

ORD-Eintrag
ord-a78277bd37c74358849646f6dbe02caa
Quelldatensatz
uspto-grants-1991_05
Patentnummer
US05013842

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