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15. Most analytical and experimental techniques were previously described.11 Only the two last key steps leading to
tritium labelled ME were described in detail. High-resolution mass spectrometry was performed on a ZAB-HF
spectrometer with an acceleration potential of 8 keV using polyethylene glycol and a solution of sodium iodide in
glycerol as matrix. The radioactivity was detected on TLC plates using a linear radioactivity detector
BERTHOLD LB 2832. Liquid scintillation counting was performed on a Packard TRI-CARB 4000 series
counter with an external standard allowing quenching corrections. All intermediates as well as the ®nal 2-C-
methyl-d-erythritol 16 were found to be pure by the usual criteria (1H, 13C NMR, melting point for the crystalline
products and TLC).
16. 2,4-O-Dibenzyl-2-C-methyl-d-[1-3H]erythritol 16: To an ice-cooled solution of the aldehyde 15 (510 mg, 1.62
mmol, 1 equiv.) in isopropanol (4 ml) was added sodium borohydride (43 mg, 1.13 mmol, 0.7 equiv.). Stirring was
continued at room temperature, and after 2 h the reaction mixture was diluted with water (5 ml), treated with 0.1N
HCl and extracted with CHCl3 (4Â20 ml). The combined extracts were dried, ®ltered, concentrated, and the
residue aorded after ¯ash chromatography 2,4-O-dibenzyl-2-C-methyl-d-erythritol 16 as colourless crystals (472
mg, 92%, mp 71±72ꢀC, Rf=0.26, ethyl acetate/cyclohexane, 70:30). 1H NMR (CDCl3): ꢀ=1.25 (3H, s, CH3); 2.58
(1H, t, J1,OH=6.5 Hz, OH); 2.84 (1H, d, J3,OH=3.9 Hz, OH); 3.60 (1H, dd, J4a,4b=9.9 Hz, J3,4a=7.0 Hz, 4-Ha);
3.72 (2H, d, J1,OH=6.5 Hz, 1-H); 3.79 (1H, dd, J4a,4b=9.9 Hz, J3,4b=3.5 Hz, 4-Hb); 4.02 (1H, ddd, J3,4a=7.0 Hz,
J
3,OH=3.9 Hz, J3,4b=3.5 Hz, 3-H); 4.51 (2H, d, J=12.3 Hz, CH2Ph); 4.61 (2H, d, J=12.3 Hz, CH2Ph); 7.25±7.38
(10H, m). 13C NMR (CDCl3): ꢀ=16.22 (CH3); 64.18 (CH2); 65.10 (CH2); 70.60 (CH2); 73.33 (CH); 73.52 (CH2);