EL-TELBANI et al.
1820
Rf 0.25. IR spectrum, ν, cm–1: 1664, 1617 (C=O).
1H NMR spectrum (DMSO-d6), δ, ppm: 1.4 t (3H,
CH2CH3), 2.6 s (3H, 3′-CH3), 3.1 s and 3.2 s (3H each,
NCH3), 4.0 q (2H, OCH2), 8.2 s (1H, 3-H). Mass spec-
trum: m/z 309 [M]+. Found, %: C 46.4; H 4.7; N 22.4;
S 10.2. C12H15N5O3S. Calculated, %: C 46.6; H 4.9;
N 22.6; S 10.4. M 309.28.
9.1 Hz), 4.20 m (2H, 3b-H, 6a′-H), 5.22 d (1H, 1b-H,
J1,2 = 9.2 Hz), 5.77 d.d (1H, 2b-H, J1,2 = J2,3 = 9.2 Hz),
6.30 d (1H, 1a-H, J1,2 = 9.4 Hz), 6.7 m (1H, PhCH),
7.4–7.8 m (5H, C6H5). Found, %: C 51.00; H 4.8;
N 6.1. C38H44N4O19S. Calculated, %: C 51.12; H 4.96;
N 6.27.
REFERENCES
Phenyl([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-
yl)methyl 6-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyr-
anosyl)-2,3,4-tri-O-acetyl-β-D-glucopyranoside (XIa)
and 3-methyl-4-oxo-4H-[1,3,4]thiadiazolo[2,3-c]-
[1,2,4]triazin-7-yl(phenyl)methyl 6-O-(2,3,4,6-tetra-
O-acetyl-β-D-glucopyranosyl)-2,3,4-tri-O-acetyl-β-
D-glucopyranoside (XIb) (general procedure).
A mixture of 10 mmol of D-Amygdalin (X) and
10 mmol of compound I or II in ethanol containing
a catalytic amount of piperidine was heated for 12 h
under reflux. The mixture was then evaporated to dry-
ness, 30 ml of pyridine and 20 ml of acetic anhydride
were added to the residue, and the mixture was stirred
for 10 h at room temperature. The mixture was evapo-
rated with addition of toluene, the residue was dis-
solved in chloroform, and the solution was washed in
succession with hydrochloric acid, a saturated solution
of sodium hydrogen carbonate (50 ml), and water (3×
50 ml), dried over anhydrous sodium sulfate, and evap-
orated. The residue was purified by column chroma-
tography using hexane–ethyl acetate (1:1) as eluent
(XIa, Rf 0.3; XIb, Rf 0.5).
1. Berk, B., Aktay, G., Yesilada, E., and Ertan, M.,
Pharmazie, 2001, vol. 56, no. 8, p. 613.
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6. Bano, Q., Tiwari, N., Giri, S., and Nizamuddin, Indian
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7. Yakout, El-S.M.A., Allam, Y.A., and Nawwar, G.A.M.,
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for Crop Improvement and Pest Management, Oxford:
Pergamon, 1987, 3rd ed.
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14. Nawwar G.A.M. and Shafik, N.A., Collect. Czech.
Chem. Commun., 1995, vol. 60, p. 2200.
15. Swellem, R.H., Allam, Y.A., and Nawwar, G.A.M.,
Compound XIa. Yield 57%, white powder,
mp 130–132°C. H NMR spectrum (CDCl3), δ, ppm:
1
1.88–2.1 (21H, CH3CO), 3.55 d.d (1H, 4a-H, J3,4
=
J4,5 = 9.1 Hz), 3.61 d.d (1H, 2a-H, J1,2 = J2,3 = 9.5 Hz),
3.67–3.72 m (5H, 6b-H, 6b′-H, 5a-H, 4b-H, 6a-H),
3.88 m (1H, 5b-H), 4.00 d.d (1H, 3a-H, J2,3 = 9.5,
J3,4 = 9.2 Hz, H-3a), 4.15 m (2H, 3b-H, 6a′-H), 5.30 d
(1H, 1b-H, J1,2 = 9.1 Hz), 5.69 d.d (1H, 2b-H, J1,2
=
J2,3 = 9.1 Hz), 6.12 d (1H, 1a-H, J1,2 = 9.5 Hz), 6.6 m
(1H, PhCH), 7.2–7.5 m (5H, C6H5), 9.1 s (1H, CH=N).
Found, %: C 50.70; H 4.8; N 6.5.C36H42N4O18S. Cal-
culated, %: C 50.82; H 4.97; N 6.58 %.
Z. Naturforsch., Teil B, 1999, vol. 54, p. 1197.
16. Frohberger, P.E. and Wiegand, C., 1966, FRG Patent
Appl. no. 1209799; Chem. Abstr., 1966, vol. 64,
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17. Brown, H.D., Matzuk, A.R., Ilves, I.R., Peterson, L.H.,
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Campbell, W.C., and Cuckler, A.C., J. Am. Chem. Soc.,
1961, vol. 83, p. 1764.
Compound XIb. Yield 52%, pale yellow crystals,
1
mp 152–154°C. H NMR spectrum (CDCl3), δ, ppm:
1.9–2.2 (21H, CH3CO), 2.5 s (3H, CH3), 3.40–3.70 m
(7H, 4a-H, 2a-H, 6b-H, 6b′-H, 5a-H, 4b-H, 6a-H),
3.9 m (1H, 5b-H), 4.1 d.d (1H, 3a-H, J2,3 = 9.4, J3,4
=
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 43 No. 12 2007