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Mironov et al.
diacetoxyiodobenzene (298 mg, 0.91 mmol) were added to a
solution of triacetylgalactal 1 (120.9 mg, 0.44 mmol) in DMF
(3 mL). The reaction was accompanied by vigorous gas evoluꢀ
tion. The suspension was stirred until the starting galactal was
consumed completely (120 h), diluted with CH2Cl2, and poured
into a saturated solution of NaHCO3. The organic layer was
separated. The aqueous layer was washed three times with
CH2Cl2. The combined organic layers were filtered through cotꢀ
ton and evaporated to dryness. The residue was separated by
column chromatography in toluene—ethyl acetate to give comꢀ
pound 16 (94 mg, 45%), Rf 0.39 (toluene—ethyl acetate, 5 : 1),
[α]D +9.5 (c 1.0, EtOAc). Further elution gave compound 4
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1
(101 mg, 47%). H NMR (CDCl3), δ: 7.50—7.60 (m, 2 H, Ar);
7.30—7.40 (m, 3 H, Ar); 2.23, 2.11, 2.08 (all s, 9 H, Ac).
13C NMR (CDCl3), δ: 169.5—170.0 (C=O); 128.1—136.6 (Ar);
20.5—20.7 (CH3C=O). Found (%): C, 45.92; H, 4.57; N, 8.82;
Se, 16.98. C18H21N3O7Se. Calculated (%): C, 45.97; H, 4.50;
N, 8.93; Se, 16.79.
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This work was financially supported by the Russian
Foundation for Basic Research (Project No. 07ꢀ03ꢀ00225).
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Received November 27, 2008;
in revised form January 29, 2009