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Witczak, Z. J.; Czernecki, S. Adv. Carbohydr. Chem. Biochem. 1998, 53,
143–199.
isoselenourea 46 as an amorphous solid (122 mg, 50%). Rf 0.43 (1:1
20
hexane–EtOAc); [
a]
þ60 (c 1.1, CH2Cl2); IR nmax 3472, 2923, 1750,
D
1610, 1494, 1347, 1225, 1043, 736 cmꢁ1; 1H NMR (300 MHz, CDCl3)
d
8.45 (d, 1H, J2,NH¼8.3 Hz, NH), 8.25 (m, 2H, Ar–Ho), 7.96 (m, 2H,
Ar–Ho0), 7.64 (m, 1H, Ar–Hp0), 7.52 (m, 1H, Ar–Hp), 7.50 (m, 2H, Ar–
Hm0), 7.46 (m, 2H, Ar–Hm), 6.03 (d, 1H, J1,2¼8.8 Hz, H-1), 5.50 (t, 1H,
J2,3¼J3,4¼9.8 Hz, H-3), 5.27 (t, 1H, J4,5¼9.6 Hz, H-4), 5.03 (m, 1H, H-
2), 4.40 (dd, 1H, J5,6a¼4.7 Hz, J6a,6b¼12.5 Hz, H-6a), 4.18 (dd, 1H,
J5,6b¼2.3 Hz, H-6b), 4.01 (s, 2H, CH2), 3.99 (ddd, 1H, H-5), 2.14, 2.08,
1.98, 1.94 (4s, 3H each, 4ꢂAc). 13C NMR (75.5 MHz, CDCl3)
d 200.2
(PhCOCH2), 176.7 (N]C–Se), 170.8, 170.6, 169.7, 169.2 (4ꢂCO), 168.0
(PhCON),135.7,134.5 (Ar–C),134.6 (Cp0),132.7 (Cp),130.1 (Co),129.2
(Co0, Cm0), 128.4 (Cm), 92.7 (C-1), 73.2 (C-3, C-5), 68.1 (C-4), 61.9
(C-6), 57.5 (C-2), 28.7 (CH2), 20.9 (ꢂ2), 20.8 (ꢂ2) (4ꢂCH3CO). LSIMS
80
m/z 677 ([MþH]þ, 50%); HRLSI-MS m/z calcd for C30H33N2NaO Se,
11
[MþH]þ: 677.1250, found: 677.1242.
3.15. 5-Benzoyl-4-phenyl-2-(1,3,4,6-tetra-O-acetyl-b-D-
12. (a) McGarrigle, E. M.; Myers, E. L.; IIIa, O.; Shaw, M. A.; Riches, S. L.; Aggarwal,
V. K. Chem. Rev. 2007, 107, 5841–5883; (b) Braga, A. L.; Lu¨dtke, D. S.; Vargas, F.
Curr. Org. Chem. 2006, 10, 1921–1938; (c) Tiecco, M.; Testaferri, L.; Bagnoli, L.;
Scarponi, C.; Temperini, A.; Marini, F.; Santi, C. Tetrahedron: Asymmetry 2006, 17,
2768–2774.
13. (a) Braverman, S.; Cherkinsky, M.; Birsa, M. L. Sci. Synth. 2005, 18, 65–320;
(b) FujiwaraꢁI., S.; Kambe, N.; Sonoda, N. In Organoselenium Chemistry, A
Practical Approach; Back, T. G., Ed.; Oxford University Press: 1999; pp 223–
240; (c) Petrov, M. L.; Zmitrovich, N. I. Russ. J. Gen. Chem. 1999, 69, 245–
256.
14. (a) Garud, D. R.; Makimura, M.; Ando, H.; Ishihara, H.; Koketsu, M. Tetrahedron
Lett. 2007, 48, 7764–7768; (b) Koketsu, M.; Yamamura, Y.; Aoki, H.; Ishihara, H.
Phosphorus, Sulfur Silicon Relat. Elem. 2006, 181, 2699–2708; (c) Barton, D. H. R.;
Parekh, S. I.; Tajbakhsh, M.; Theodorakis, E. A.; Tse, C.-L. Tetrahedron 1994, 50,
639–654.
15. Koketsu, M.; Ishihara, H. Curr. Org. Synth. 2006, 3, 439–455.
16. (a) Heimgartner, H.; Zhou, Y.; Atanassov, P. K.; Sommen, G. L. Phosphorus, Sulfur
Silicon Relat. Elem. 2008, 183, 840–855; (b) Sommen, G. L.; Linden, A.; Heim-
gartner, H. Helv. Chim. Acta 2008, 91, 209–219; (c) Garud, D. R.; Koketsu, M.;
glucopyranos-2-yl)amino-1,3-selenazole (47)
To
a solution of Se-phenacyl isoselenourea 46 (61 mg,
0.09 mmol) in EtOH (4 mL) was added AcOH (0.4 mL) and the
resulting mixture was refluxed in the darkness for 1.5 h. Then, it
was concentrated to dryness and the residue was purified by col-
umn chromatography (CH2Cl2/100:1 CH2Cl2–MeOH) to give 47 as
a syrup (46 mg, 79%); Rf 0.39 (40:1 CH2Cl2–MeOH); [
20
a
]
ꢁ10 (c 1.0,
D
CH2Cl2); IR nmax 2926, 1752, 1544, 1467, 1372, 1326, 1220, 1040,
707 cmꢁ1
; d 8.83 (d, 1H,
1H NMR (500 MHz, DMSO-d6)
0
J2 ,NH¼8.7 Hz, NH), 7.33 (m, 2H, Ar–Ho), 7.28 (m, 1H, Ar–Hp), 7.24
(m, 2H, Ar–Ho0), 7.15 (m, 1H, Ar–Hp0), 7.11 (m, 2H, Ar–Hm0), 7.07 (m,
2H, Ar–Hm), 5.96 (d, 1H, J1 ,2 ¼8.3 Hz, H-10), 0 5.41 (t, 1H,
0
0
0
0
0
0
0
0
0
J2 ,3 ¼J3 ,4 ¼9.7 Hz, H-3 ), 4.99 (t,1H, J4 ,5 ¼9.7 Hz, H-4 ),04.20 (dd,1H,
0
0
0
0
0
J5 ,6a ¼4.5 Hz, J6a ,6b ¼12.4 Hz, H-6a ), 4.18 (m, 1H, H-2 ), 4.12 (ddd,
Ishihara, H. Molecules 2007, 12, 504–535.
0
0
0
0
´
1H, J5 ,6b ¼2.1 Hz, H-5 ), 4.01 (dd,1H, H-6b ), 2.05, 2.01,1.99,1.90 (4s,
´
˜
´
17. Fernandez-Bolanos, J. G.; Lopez, O.; Ulgar, V.; Maya, I.; Fuentes, J. Tetrahedron
Lett. 2004, 45, 4081–4084.
12H, 4ꢂAc); 1H NMR (500 MHz, CDCl3)
d 7.44 (m, 2H, Ar–Ho), 7.31
18. (a) Koketsu, M.; Suzuki, N.; Ishihara, H. J. Org. Chem. 1999, 64, 6473–6475; (b)
Suzuki, H.; Usuki, M.; Hanafusa, T. Synthesis 1979, 705–707; (c) Henriksen, L.;
Ehrbar, U. Synthesis 1976, 519–521.
(m, 2H, Ar–Ho0), 7.23 (m, 1H, Ar–Hp), 7.13 (m, 1H, Ar–Hp0), 7.07 (m,
4H, Ar–Hm0, Ar–Hm),05.62 (d, 1H, J1 ,2 ¼8.5 Hz, H-1 ), 5.16 (t, 1H,
0
0
0
0
0
0
0
0
0
0
19. Jensen, K. A.; Frederiksen, E. Z. Anorg. Allg. Chem. 1936, 230, 31–33.
20. (a) Krishnaswamy, D. Synlett 2000, 1860; (b) Cotarca, L.; Delogu, P.; Nardelli, A.;
J2 ,3 ¼J3 ,4 ¼9.6 Hz, H-3 ), 5.11 (t, 1H, J4 ,5 ¼9.6 Hz, H-4 ), 4.29 (dd, 1H,
0
0
0
0
0
0
0
J5 ,6a ¼4.5 Hz, J6a ,6b ¼12.5 Hz, H-6a ), 4.08 (dd, 1H, J5 ,6b ¼2.2 Hz, H-
ˇ
Sunjic´, V. Synthesis 1995, 553–576.
6b0), 3.78 (br t, 1H, H-20), 3.68 (ddd, 1H, H-50), 2.11, 2.10, 2.04 (ꢂ2)
21. Su, W. K.; Liang, X. R. J. Indian Chem. Soc. 2003, 80, 645–647.
22. Koketsu, M.; Sakai, T.; Kiyokuni, T.; Garud, D. R.; Ando, H.; Ishihara, H. Het-
erocycles 2006, 68, 1607–1615.
23. Krishnamurthy, S. Tetrahedron Lett. 1982, 23, 3315–3318.
24. Zhou, Y.; Denk, M. K. Tetrahedron Lett. 2003, 44, 1295–1299.
25. Ishihara, H.; Koketsu, M.; Fukuta, Y.; Nada, F. J. Am. Chem. Soc. 2001, 123, 8408–
8409.
26. Koketsu, M.; Fukuta, Y.; Ishihara, H. Tetrahedron Lett. 2001, 42, 6333–6335.
27. Ha, S. K.; Koketsu, M.; Lee, K.; Choi, S. Y.; Park, J.-H.; Ishihara, H.; Kim, S. Y. Biol.
Pharm. Bull. 2005, 28, 838–840.
28. (a) Tsukagoshi, H.; Koketsu, M.; Kato, M.; Kurabayashi, M.; Nishina, A.; Kimura, H.
FEBS J. 2007, 274, 6046–6054; (b) Misra, B.; Maity, D. K.; Priyadarsini, K. I.; Mohan,
H.; Mittal, J. P. J. Phys. Chem. A 2004, 108, 1552–1559.
(3s, 3H each, 4ꢂAc); 13C NMR (75.5 MHz, CDCl3)
d 190.5 (PhCO),
172.9 (C-2), 170.8, 170.7, 169.5, 169.0 (4ꢂCO), 158.2 (C-4), 138.0,
135.2 (Ar–C), 131.6 (Cp), 130.3 (Co0), 129.3 (Co), 128.9, 128.8 (Cp0, C-
5), 127.9, 127.8 (Cm, Cm0), 92.8 (C-10), 73.1 (C-30), 72.9 (C-50), 67.9 (C-
40), 61.6 (C-60), 61.3 (C-20), 21.2, 21.0, 20.9, 20.7 (4ꢂCH3CO); LSIMS
80
m/z 659 ([MþH]þ, 10%); HRLSI-MS m/z calcd for C30H31N2O Se,
10
[MþH]þ: 659.1144, found: 659.1151.
Acknowledgements
29. (a) Koketsu, M.; Ishihara, H. Curr. Org. Chem. 2003, 7, 175–185; (b) Atanassov, P.
K.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 2003, 86, 3235–3243.
30. Somsa´k, L.; Felfoeldi, N.; Konya, B.; Huese, C.; Telepo, K.; Bokor, E.; Czifrak, K.
Carbohydr. Res. 2008, 343, 2083–2093.
´
´
We thank the Direccion General de Investigacion of Spain (Grant
´
CTQ 2005-01830/BQU) and the Junta de Andalucıa (FQM 134) for
31. Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York,
NY, 1994; p 1197.
financial support.
´
´
˜
32. Lopez, O.; Maya, I.; Fuentes, J.; Fernandez-Bolanos, J. G. Tetrahedron 2004, 60,
61–72.
Supplementary data
33. Witczak, Z. J. Tetrahedron 1985, 41, 4781–4785.
34. Babiano Caballero, R.; Fuentes Mota, J.; Galbis Pe´rez, J. A. Carbohydr. Res. 1986,
154, 280–288.
Supplementary data associated with this article can be found in
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