Compound 1

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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

2-Aminooxazole (4; 8.4 mg, 0.1 mmol) was added to a suspension of aminal 8b (27 mg, 0.1 mmol) in D₂O (1 mL). The reaction was adjusted to pD 7 using dilute DCl/NaOD and stirred at 40 °C. After 22 h the reaction was homogenous, and ¹H NMR spectra were acquired (Supplementary Figure 30). Complete conversion of aminal 8b to a diastereoisomeric mixture of pentose aminooxazolines (1) (ribo-1 (44%), arabino-1 (32%), xylo-1 (10%), f-lyxo-1 (4%), p-lyxo -1 (11%)) and quantitative liberation of 2-aminothiazole (7) were observed. Branched apiose aminooxazolines 5 and dihydroxyacetone (2q) were not observed within the limits of detection. The results are summarised in Supplementary Table 11 (row 2). Data for pentose aminooxazolines (1) (Supplementary Figure 30): ¹H NMR (600 MHz, D₂O) xylo-1 δ 5.86 (d, J = 5.2 Hz, 1H, (C1')–H); arabino-1 δ 5.83 (d, J = 5.6 Hz, 1H, (C1')–H); ribo-1 δ 5.72 (d, J = 5.1 Hz, 1H, (C1')–H); f-lyxo-1 δ 5.66 (d, J = 5.6 Hz, 1H, (C1')–H); p-lyxo-1 δ 5.43 (d, J = 5.8 Hz, 1H, (C1')–H).