Compound 7

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InChIKey XRWZIAQTASKZRO-WJKHNNNCSA-N

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

A mixture of CuSO₄.5H₂O (15 mg, 94 μmol), sodium ascorbate (30 mg, 152 μmol), 5 (367 mg, 157 μmol) and 6 (412 mg, 1.89 mmol) in THF/H₂O (7 mL, 1:1) was heated 2 h under microwave irradiation (100°C). The product was precipitated by addition of MeOH (20 mL). The precipitate was washed with MeOH and dried under reduced pressure. Gel permeation chromatography (Sephadex G-50, H₂O/MeOH; 90:10) gave 7 (647 mg, 91%). Orange powder. IR (neat): 3308 (OH), 1738 (C=O). ¹H NMR (400 MHz, D₂O), δ: 8.05 (m, 10H), 4.80 (m), 4.43 (m), 3.75 (m), 2.25 (m), 1.16 (m), 0.15 (s, 9H, TMS). ¹³C NMR (100 MHz, D₂O), δ: 163.8 (broad), 145.6 (broad), 141.2 (broad), 125.1 (broad), 99.6, 73.0, 70.7, 70.1, 66.7, 64.6, 60.9, 58.3, 47.6, 45.6, 38.9, 31.8, 28.7, 13.7, 0.1. MALDI-MS: 4465.6 (8%, [M-TMS+Na]⁺, calcd for C₂₀₅H₂₁₆O₈₄N₃₀Na: 4465.3), 4120.5 (8%, [M-1/2 malonate+Na]⁺, calcd for C₁₉₂H₁₉₇O₇₆N₂₇Na: 4119.2), 3759.4 (34%, [M-1 malonate+Na]⁺, calcd for C₁₇₈H₁₇₇O₆₈N₂₄Na: 3761.1), 3414.2 (26%, [M-1 malonate-1/2malonate+Na]⁺, calcd for C₁₆₅H₁₅₇O₆₀N₂₁Na: 3415.0), 3054.2 (36%, [M-2 malonates+Na]⁺, calcd for C₁₅₁H₁₃₆O₅₂N₁₈Na: 3056.8), 2708.9 (21%, [M-2 malonates-1/2malonate+Na]⁺, calcd for C₁₃₈H₁₁₇O₄₄N₁₅Na: 2710.7), 2349.7 (17%, [M-TMS-3 malonates+Na]⁺, calcd for C₁₂₄H₉₇O₃₆N₁₂Na: 2352.6), 2003.6 (8%, [M-3 malonates-1/2malonate+Na]⁺, calcd for C₁₁₁H₇₇O₂₈N₉Na: 2006.5), 1644.4 (6%, [M-4 malonates+Na]⁺, calcd for C₉₇H₅₇O₂₀N₆Na: 1648.3).