Angewandte
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[18] The anomer ratio of compound 17 (at the newly formed
anomeric position) was determined to be a/b = 67:33 by NMR
spectroscopic analysis.
[19] Compound 21 was identified by comparison of the spectroscopic
data of the debenzylation product with those of an authentic
sample: S. Koto, N. Morishima, S. Shichi, H. Haigoh, M.
Hirooka, M. Okamoto, T. Higuchi, K. Shimizu, Y. Hashimoto,
T. Irisawa, H. Kawasaki, Y. Takahashi, M. Yamazaki, Y. Mori, K.
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[
[
[
3] D. P. Curran, Pure Appl.Chem. 2000, 72, 1649; D. P. Curran,
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174, and references therein; Corrigendum: D. P. Curran,
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[
[
[
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6
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1
1
[
[
[
10] T. Miura, T. Inazu, Tetrahedron Lett. 2003, 44, 1819.
11] Product mixtures containing the fluorous compounds 10, 13, and
20 were partitioned between FC-72 and MeOH. Those contain-
ing the fluorous compounds 11 and 18 were partitioned between
FC-72, toluene, and water. The product mixture containing the
fluorous compound 17 was partitioned between FC-72 and
acetonitrile. None of the fluorous compounds were detected by
TLC of the organic layer after three extractions with FC-72,
which shows that these compounds were quantitatively extracted
with FC-72.
[
12] The anomer ratio of compound 13 (at the newly formed
anomeric position) was determined to be a/b = 50:50 by NMR
spectroscopic analysis.
[
[
[
13] R. R. Schmidt, J. Michel, M. Roos, Liebigs Ann.Chem. 1984,
1343.
14] EtOC F is a commercially available fluorocarbon solvent (3m,
4
9
Tokyo) called Novec HFE-7200.
15] FC-72 is a commercially available fluorocarbon solvent (3m,
Tokyo) called Fluorinert FC-72, which consists of perfluorohex-
ane (C F ) isomers.
6
14
[
[
16] Compound 14 was identified by comparison of spectroscopic
data of the debenzylated products (melibiose and allolactose)
with those of authentic samples: K. Bock, C. Pedersen, H.
Pedersen, Adv.Carbohydr.Chem.Biochem.
1983, 42, 193; K.
Ajisaka, H. Fujimoto, H. Nishida, Carbohydr.Res. 1988, 180, 35.
17] W. Xu, S. A. Springfield, J. T. Koh, Carbohydr.Res. 2000, 325,
169.
Angew. Chem. Int. Ed. 2003, 42, 2047 – 2051
ꢀ 2003 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
2051