Compound 8c

(2R,3S)-4,4-bis(thiazol-2-ylamino)butane-1,2,3-triol

From: Prebiotic selection and assembly of proteinogenic amino acids and natural nucleotides from complex mixtures

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Compound data: CIF

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

Prepared according to the general procedure outlined in 8. 1H NMR (600 MHz, DMSO-d6) δ 7.84 (d, J = 7.9 Hz, 1H, NH), 7.73 (d, J = 7.9 Hz, 1H, NH), 7.03 (d, J = 3.7 Hz, 1H, Ar), 7.02 (d, J = 3.7 Hz, 1H, Ar), 6.65 (d, J = 3.7 Hz, 2H, Ar), 5.64 (td, J = 7.9, 1.9 Hz, 1H, (C1')–H), 5.49 (d, J = 5.8 Hz, 1H, OH), 5.25 (br. d, J = 3.0 Hz, 1H, OH), 4.39 (t, J = 5.0 Hz, 1H, OH), 3.62 (m, 2H, (C2')–H, (C4')–H), 3.42 (m, 1H, (C3')–H), 3.30–3.34 (m, 1H, (C4')–H). 1H NMR (600 MHz, DMSO-d6 + D2O) δ 7.03 (d, J = 3.6 Hz, 1H, Ar), 7.02 (d, J=3.6 Hz, 1H, Ar), 6.65 (d, J = 3.6 Hz, 2H, Ar), 5.61 (d, J = 1.3 Hz, 1H, (C1')–H), 3.60 (obs., 2H, (C2')–H, (C4')–H), 3.41 (dd, J = 11.3, 6.0 Hz, (C3')–H), 3.32 (ddd, J = 8.8, 6.0, 2.8 Hz, 1H, (C4')–H). 13C NMR (151 MHz, DMSO-d6) δ 168.6*, 167.6*, 138.4*, 137.8*, 107.4*, 107.3*, 72.5, 71.3, 66.1, 62.9 (*diastereotopic resonance). HRMS ESI–TOF [M + H]+ cal. for C10H14O3N4S2 303.0586; obs. 303.0588. IR (solid, cm-1): 3357, 3210, 3011, 2887, 1551, 1523, 1476, 1308, 1280. M.p. 120–125 °C (decomp.). Single crystal X-ray structure (CCD 1477043; Supplementary Figure 156).

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