Water → 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol

Beteiligte Stoffe

Reaktionsschritte

3-O-Benzyl-N-benzyloxycarbonyl-2,6-imino-2,5,6-trideoxy-D-lyxo-hexose (24) (364 mg, 0.986 mmol) was dissolved in ethanol (5 ml) and treated with a solution of sodium borohydride (30.0 mg, 0.784 mmol) in a 1:1 mixture of EtOH and H2O (2 ml). After 20 minutes excess ammonium chloride was added, the solution concentrated, poured into brine (15 ml) and extracted with dichloromethane (4×20 ml). The organic layers were combined, dried, filtered and evaporated to give 4-O-benzyl-N-benzyloxycarbonyl-1,5-imino-1,2,5-trideoxy-D-arabino-hexitol (355 mg, 97%) as a clear oil, [α]20D -36.7° (c, 0.22 in chloroform); νmax (film) 3380 (OH), 2910, 1665 (2×CO), 1430, 1210 and 1075 cm-1 ; 1H NMR δ 1.55-1.68 (1H, m, H-2); 2.04-2.17 (1H, m, H-2'); 2.85 (2H, bs, 2×OH); 3.40-3.57 (2H, m, H-5, H-1); 3.83-4.03 (4H, m, 6,6'-H, H-4, H-1'); 4.34 (1H, bs, H-3); 4.55, 4.72 (2H, 2×d, CH2Ph, JH,H 12.0 Hz); 5.15 (2H, s, CH2 -Z); 7.28-7.38 (10, m, 2×H-Ph). m/z: 264 (M-benzyloxy+, 100%), 91 (10%), 372 (M+H+, 5%).

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