GLYCOSYLATED DERIVATIVES OF SUBSTITUTED HYDROXYLAMINE
433
2. Davis, B.G., J. Chem. Soc. Perkin Trans., 2000,
(
с
1.0, chloroform). Published [13]: 76%, mp 201.7–
pp. 2137–2160.
203.2 С (CH2Cl2/ether), α]D –44.7° (chloroform).
°
[
3. Hanessian, S., Bacquet, C., and Lehong, N., Carboꢀ
hydr. Res., 1980, vol. 80, pp. C17–C22.
General procedure for the synthesis of glycosides
(VIa–h). A mixture of glycoside (IIIa) (0.300 g,
0.647 mmol), the corresponding alcohol (0.970 mmol),
and anhydrous cobalt(II) chloride (0.336 g, 2.586 mmol)
in anhydrous methylene chloride (10 mL) was stirred
4. Hanessian, S., Preparative Carbohydrate Chemistry
,
New York: Marcel Dekker, 1997, pp. 381–412.
5. Hanessian, S. and Lou, B., Chem. Rev., 2000, vol. 100,
under reflux on an oil bath at 50°С up to the total conꢀ
pp. 4443–4463.
version of the glycosyl donor (IIIa) (TLC monitoring
in systems (1) and (2)). The reaction mixture was filꢀ
tered off from the solid phase, and the precipitate was
6. PistiaꢀBrueggeman, G. and Hollingsworth, R.I., Carꢀ
bohydr. Res., 2003, vol. 338, pp. 455–458.
washed on a filter with methylene chloride (
2
×
5 mL).
7. Koide, K., Ohno, M., and Kobayashi, S., Tetrahedron
Lett., 1991, vol. 32, pp. 7065–7068.
The filtrate was washed with water ( mL) and the
3 5
×
organic layer was dried with anhydrous sodium sulfate.
Methylene chloride was evaporated on a rotor evapoꢀ
rator to dryness at a bath temperature as low as 40°С.
8. Chang, C.ꢀW. and Ho, T.ꢀL., J. Chinese Chem. Soc.
2006, vol. 53, pp. 1567–1570.
,
The target products were isolated by column chromaꢀ
tography.
9. Chupakhina, Т.А., Kuryanov, V.O., Chirva, V.Ya.,
Grigorash, R.Ya., Коtlyar, S.А., Кamalov G.L, Russ. J.
Bioorg. Chem., 2004, vol. 30, pp. 301–303.
Heptylꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀ
Dꢀglucopyranoside (VIa), mp 120–123
1.0, chloroform). For the published data, see [18].
O
ꢀacetylꢀ2ꢀdeoxyꢀ
β
ꢀ
°
С, [ 546 –16
α
]
°
10. Kur’yanov, V.O., Chupakhina, T.A., and Chirva, V.Ya.,
Zh. Org. Farm. Khim., 2009, vol. 7, pp. 57–63.
(с
11. Kur’yanov, V.O., Katsev, A.M., Chupakhina, T.A., and
Chirva, V.Ya., Zh. Org. Farm. Khim., 2009, vol. 7,
pp. 30–40.
Isopropylꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀOꢀacetylꢀ2ꢀdeoxyꢀ
β
ꢀDꢀglucopyranoside (VIb), mp167–169 С, [
°
α]
546
⎯6° (с
1.0, chloroform).
12. Kuryanov, V.O., Chupakhina, T.A., Shapovalova, A.A.,
Katsev, A.M., and Chirva, V.Ya., Russ. J. Bioorg. Chem.,
2011, vol. 37, pp. 231–239.
Octadecylꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀ
Dꢀglucopyranoside (VIc), mp 102–104
1.0, chloroform). Published [17]: mp 102–
С, [ 546 –7.3 1.0, chloroform).
O
ꢀacetylꢀ2ꢀdeoxyꢀ
β
ꢀ
°С, [
α]
546
⎯
104
7° (с
13. Cao, S., Tropper, F.D., and Roy, R., Tetrahedron, 1995,
°
α]
° (с
vol. 51, pp. 6679–6686.
(3ꢀPhenylpropyl)ꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀ
O
ꢀacetylꢀ
ꢀDꢀglucopyranoside (VId), mp 136 С,
1.0, chloroform).
14. Lemieux, R.U., Pure. Appl. Chem., 1971, vol. 25,
2ꢀdeoxyꢀ
β
°
pp. 527–548.
[
α]546 –3
°
(с
15. Vankar, D., Vankar, P.S., Behrendt, M., and Schmidt, R.R.,
(3ꢀBenzyloxypropyl)ꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀ
acetylꢀ2ꢀdeoxyꢀ ꢀDꢀglucopyranoside (VIe), mp 87–
90 С, [ 546 –17 1.0, chloroform).
Oꢀ
Tetrahedron, 1991, vol. 47, pp. 9985–9992.
β
16. Zemlyakov, A.E., Tsikalova, V.N., Zemlyakov, S.A.,
and Chirva, V.Ya., Uchen. Zap. TNU Im. V.I. Vernadꢀ
skogo, Ser. Biol. Khim., 2010, vol. 23 (62), pp. 225–231.
°
α]
° (с
6ꢀ ꢀ(2ꢀAcetamidoꢀ3,4,6ꢀtriꢀ
O
Oꢀacetylꢀ2ꢀdeoxyꢀ ꢀ
β
Dꢀglucopyranosyl)ꢀ1,2:3,4ꢀdiꢀ
galactopyranose (VIf), mp 117–121
O
ꢀisopropylideneꢀ
α
ꢀDꢀ
17. Zemlyakov, A.E., Kuryanov, V.O., Sidorova E.A., and
Chirva, V.Ya., Russ. J. Bioorg. Chem., 1998, vol. 24,
pp. 551–558.
°
С, [α]
546
–75°
(с
1.0, chloroform).
Cholesterylꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀ
deoxyꢀ ꢀDꢀglucopyranoside (VIg), mp 206
–27 1.0, chloroform). Published [17, 21]: mp
206 546 –27 0.38, chloroform).
O
ꢀacetylꢀ2ꢀ
18. Zemlyakov, A.E. and Chirva, V.Ya., Khim. Prirodn.
Soed., 1987, no. 5, pp. 714–718.
β
°С, [
α]
546
° (с
19. Kur’yanov, V.O., Zemlyakov, A.E., and Chirva, V.Ya.,
Russ. J. Bioorg. Chem., 1996, vol. 22, no. 4, pp. 243–
246.
°
С, [
α
]
° (с
Cyclohexylꢀ2ꢀacetamidoꢀ3,4,6ꢀtriꢀOꢀacetylꢀ2ꢀdeoxyꢀ
β
ꢀDꢀglucopyranoside (VIh), mp 179
1.0, chloroform). Published [17]: mp 179
–17.6 0.77, chloroform).
°
С, [
α
]
–18°
546
20. Zhdanov, Yu.A., Dorofeenko, G.N., Korol’chenko, G.A.,
and Bogdanova, G.V., Praktikum po khimii uglevodov
(Carbohydrate Chemistry: A Practical Course),
Zhdanov, Yu.A., Ed., Moscow: Vysshaya shkola, 1973.
546
С, [ ]
(с
°
α
° (с
21. Horton, D., Methods in Carbohydrate Chemistry, Vol. 6,
Whistler. R.L. and Bemiller, J.N., Eds., New York:
Academic Press, 1972.
REFERENCES
1. Schmidt, R.R., CastroꢀPalomino, J.C., and Retz, O.,
Translated by E. Shirokova
Pure Appl. Chem., 1999, vol. 71, pp. 729–744.
RUSSIAN JOURNAL OF BIOORGANIC CHEMISTRY Vol. 39
No. 4
2013