SYNTHESIS OF 6-BROMO-6-DEZOXY- -CYCLODEXTRIN
1959
(
62%) of compound III, mp 220 223 C (decomp.).
33083a) and Grant of President of Russian Federation
for supporting the leading scientific schools (no. NSH-
5515.2006.3).
1
H NMR spectrum (DMSO-d ), , ppm, (J, Hz):
6
6
3
2
3
.34 d.d (7H, H , J
5
6
9.86, J
6
6
14.26), 3.41 d
H H
H H
2
3
6
3
(
7H, H , J
1
2
4.02), 3.66 d.d (7H, H , J
5
6
9.87,
H H
H H
REFERENCES
2
4
3
3
J
6
6
14.26), 3.71 d.d (7H, H , J
4
5
9.14, J
H H
3 4
H H
H H
5
3
3
1
0.23), 3.85 m (7H, H , J
4
5
9.14, J
5
6
9.87,
9.87), 4.98 d (7H,
H H
1. Khan, A.R., Forgo, P., Stine, K.J., and D’Souza, V.T.,
H H
3 3
3 4
H H
3
Chem. Rev., 1998, vol. 98, no. 5, p. 1977.
J
5
6
9.86), 3.99 d (7H, H , J
H H
1
3
2
H , J
1
2
4.02), 5.89 d (7H, C OH), 6.03 d (7H,
H H
2. Grachev, M.K., Mustafin, I.G., and Nifant’ev, E.E., Zh.
Obshch. Khim., 1998, vol. 68, no. 9, p. 1519.
3
C OH). Found, %: C 32.53; H 4.01; Br 35.00.
C H Br O . Calculated, %: C 32.02; H 4.03; Br
4
2
63
7
28
3
. Grachev, M.K., Sipin, S.V., Kurochkina, G.I., and Ni-
fant’ev, E.E., Zh. Obshch. Khim., 2006, vol. 76, no. 6,
p. 1048.
3
5.51.
b. To a solution of 1 g (0.457 mmol) of tosyl
derivative II in 5 ml of methylene chloride and 2 ml
of pyridine, 1.93 g (4.570 mmol) of dibromotriphe-
nylphosphorane was added. Then the reaction mixture
workup was similar to the described in method a.
4
5
. Gadelle, A., and Defaye, J., Angew. Chem., 1991,
vol. 103, no. 1, p. 94.
. Gorin, B.I., Riopelle, R.J., and Thatcher G.R.J., Tetra-
hedron Lett., 1996, vol. 37, no. 27, p. 4647; Chmur-
ski, K., and Defaye, J., Tetrahedron Lett., 1997, vol. 38,
no. 42, p. 7365; Visitiu, D., Walkinshaw, C.S., Go-
rin, B.I., and Thatcher, G.R.J., J. Org. Chem., 1997,
vol. 62, no. 25, p. 8760.
Yield of compound III is 0.418 g (58%), mp 220
1
2
23 C (decomp.). The H NMR spectrum in DMSO-
d6 is identical to the listed in method a. Found, %:
C 32.58; H 4.010; Br 35.29. C H Br O . Calcu-
4
2
63
7
28
lated, %: C 32.02; H 4.03; Br 35.51.
1
The H NMR spectra were recorded on a Bruker
WP-250 spectrometer (external reference TMS).
6
. Kurochkina, G.I., Trushkin, M.K., Grachev, M.K., and
Nifant’ev, E.E., Zh. Obshch. Khim., 2004, vol. 74,
no. 10, p. 1743.
ACKNOWLEDGMENTS
This work was financially supported by Russian
Foundation for Basic Research (project no. 05-03-
7. Alker, D., Ashton, P.R., Harding, V.D., and Koniger, R.,
Tetrahedron Lett., 1994, vol. 35, no. 48, p. 9091.
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 76 No. 12 2006