SELEZNEVA et al.
914
10. Koch, H. and Fischer, F., Z. Chem., 1967, vol. 7, no. 1,
(2S,3S)-3-Benzyloxy-4-[tert-butyl(dimethyl)-
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silyloxy]butane-1,2-diol (10). Compound 9, 0.05 g
(0.15 mmol), was dissolved in 5 mL of anhydrous
methanol, 0.03 g (0.22 mmol) of freshly calcined
potassium carbonate was added, and the mixture was
stirred until compound 9 disappeared (TLC). The mix-
ture was filtered, the filtrate was evaporated, and the
residue was purified by silica gel column chromatog-
raphy using petroleum ether–ethyl acetate (1:1) as
11. Sands, B.H. and Rowland, A.T., Steroids, 1964, vol. 4,
no. 2, p. 175.
12. Vostrikov, N.S., Loza, V.V., Selezneva, N.K., and Mifta-
khov, M.S., Russ. J. Org. Chem., 2014, vol. 50, p. 140.
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1
14. Albanese, D., Landini, D., Penco, M., Tagliable, A., and
Carlini, E., Org. Process Res. Dev., 2010, vol. 14,
p. 705.
eluent. Yield 0.035 g (75%). H NMR spectrum
(300.13 MHz, CDCl3), δ, ppm: 0.003 s (6H, SiMe2),
0.82 s (9H, t-Bu), 2.59 br.s (2H, OH), 3.45 d.d (1H,
3-H, J = 4.7, 10.1 Hz), 3.59 d.d (2H, OC4H2, J = 3.6,
4.8 Hz), 3.72 m (3H, 2-H, OC1H2), 4.48 d (1H, PhCH2,
J = 11.5 Hz), 4.68 d (1H, PhCH2, J = 11.6 Hz), 7.26 m
(5H, Ph). 13C NMR spectrum (75.47 MHz, CDCl3), δC,
ppm: 5.57 (SiMe2), 18.17 (CMe3), 25.79 (CH3), 62.28
(C1), 63.62 (C4), 72.79 (PhCH2), 71.77 (C2), 79.49
(C3); 121.97, 128.14, 128.51, 137.91 (Ph).
15. Shiina, I., Shibata, J., Ibuka, R., Imai, Y., and Mukai-
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18. Jensen, F., Introduction to Computational Chemistry,
Chichester: Wiley, 1999, p. 428.
The spectral and analytical studies and quantum
chemical calculations were performed using the equip-
ment of the Khimiya Joint Center, Ufa Institute of
Chemistry, Russian Academy of Sciences.
19. Koch, W. and Holthausen, M.C., A Chemist’s Guide to
Density Functional Theory, Weinheim: Wiley-VCH,
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RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 51 No. 7 2015