1,2-Diacetoxy-di-epi-lentiginosine (19)
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Acetylation of di-epi-lentiginosine 7b (0.02 g, 0.13 mmol) with
pyridine (2 cm3), acetic anhydride (0.04 cm3, 0.38 mmol) and
DMAP (cat.) as in case of 15, after purification by column chro-
matography (n-hexane–ethyl acetate = 8 : 2) afforded diacetoxy-
di-epi-lentiginosine 19 as a thick liquid (0.025 g, 83%): (found: C,
60.01; H, 8.20. Calc. for C12H19NO4: C, 59.73; H, 7.94); Rf = 0.20
(n-hexane–ethyl acetate = 6 : 4); [a]D = −37.7 (c 0.26, CHCl3);
mmax(neat)/cm−11725, 1210; dH (300 MHz, CDCl3) 1.20–1.40 (2H,
m, H-7, H-6), 1.42–1.84 (4H, m, H-6, H-7, H-8), 2.06 (3H, s, CH3),
2.10 (3H, s, CH3), 2.12–2.27 (3H, m, H-3, H-5), 3.11 (1H, bd, J =
11.0 Hz, H-3), 3.64 (1H, dd, J = 9.9 and 7.1 Hz, H-8a), 4.99 (1H,
t, J = 7.4 Hz, H-2), 5.16 (1H, d, J = 4.6 Hz, H-1); dC (75 MHz,
CDCl3) 20.9 (strong, C-6 and C-7), 23.7 (C-8), 24.8 (CH3), 24.9
(CH3), 53.1 (C-5), 59.7 (C-3), 65.7 (C-8a), 76.9 (C-1), 78.8 (C-2),
169.9 (COCH3), 170.2 (COCH3).
Acknowledgements
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We are thankful to Dr MalaRao, Head of the Biochemical
Division, and Dr V. P. Vinod of the National Chemical laboratory
(NCL), Pune, for carrying out glycosidase inhibitory activity stud-
ies of our target molecules. We are grateful to Prof. M. S. Wadia
and Dr K. G. Marathe for helpful discussion. AKKS is thankful
to CSIR, New Delhi, for a Research Fellowship. We gratefully
acknowledge DST, New Delhi, for the research fund SR/S1/OC-
21/2005.
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