@article{26b25525523641ce9cc14da87f32f01d,
title = "Synthesis of carboranyl derivatives of alkynyl glycosides as potential BNCT agents",
abstract = "A series of amphiphilic carbohydrate-carborane hybrids consisting of a lipophilic core (carborane cage) and a glycoside moiety for conferring high- affinity recognition by the cellular lectins have been prepared in a chemically accessible fashion.",
keywords = "Boron and compounds, Carboranes, Glycosides",
author = "Giovenzana, {Giovanni Battista} and Lay Luigi and Diego Monti and Giovanni Palmisano and Luigi Panza",
note = "Funding Information: The title compound was obtained (83%) after repeated silica gel chromatography with MeOH-iPrOH-H20 6:1.5:1.5 as the eluant. Colourless foam. \[O~\]D+ 3.78 (C 1.3, CH3OH). 1H-NMR (300 MHz, CD3OD) ~i 4.46 (d, 1 H, 2j = 12.5 Hz, OCHHCcage), 4.45 (d, 1 H, Jr,2' = 7.7 Hz, H-I' or H-1), 4.36 (d, 1 H, Jl.2 = 7.2 Hz, H-I or H-I'), 4.29 (d, 1 H, 2j =12.5 Hz, OCHHCcage), 3.95-3.65 (m, 6 H), 3.65-3.37 (rn, 5 H), 3.30 (t, 1 H, J3,4 = J4.5 = 8.2 Hz, H-4). 13C-NMR (75.46 MHz, CDCI3): ~ 105.0, 103.6 (2d, C-I, C-I'), 80.5 (d), 77.8 (s, Ccage), 77.0 (d), 76.6 (d), 76.4 (d), 74.7 (d), 74.4 (d), 72.5 (d), 70.3 (d), 70.0 (t, CH2Ccage), 62.5, 61.9 (2t, C-6, C-6'), 20.7-20.3 (q, CH3CO). I1B-NMR (CD3OD) ~ -2.21 (2 B), -10.27 (8 B). IR 3050 (Vcncage), 2590 cm -1 (YAH). ESI-MS: Calcd. for C2sH56BloO22 853 u.m.a.; found: 876 u.m.a. (MNa÷). \[Found: C, 39.15; H, 6.81. C2sH56BIoO22 requires C, 39.43; H, 6.62%\]. Acknowledgement G.P. and L.P. are grateful to MURST and Universit~ del Piemonte Orientale (Fondi ex-60%) for financial support to this work and D.M. to the CNR for financial support. We would like to thank Professor S. Aime (Universit~ di Torino) for llB-NMR spectra and Dr. L. Calabi (Bracco S.p.A., Milano) for ESI-MS spectra.",
year = "1999",
month = dec,
day = "3",
doi = "10.1016/S0040-4020(99)00878-9",
language = "English",
volume = "55",
pages = "14123--14136",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Ltd.",
number = "49",
}