Arbinose-Based Synthesis
899
52. Bouali, A.; Descotes, G.; Ewing, D.F.; Grouiller, A.; Lefkidou, J.; Lespinasse, A.-D.; Mackenzie, G.
Dramatization of 1,3,4,6-tetra-O-benzyl-α-D-fructofuranose at the anomeric site: O-alkylation, O-
acylation, O-arylation, amination and selenylation. J. Carbohydr. Chem. 1992, 11(2), 159–169.
53. Martin, O.R. The unexpected intramolecular C-arylation of 2-O-benzylated cyclic sugar derivatives:
a useful 1,2-cis-C-glycosylation reaction. Tetrahedron Lett. 1985, 26(17), 2055–2058.
54. Kro¨ll, P.; Wernicke, A.; Kova´cs, J.; Lu¨tzen, A. Comprehensive reinvestigation of the reaction of
D-aldoses with Meldrum’s acid yielding mainly chain extended 3,6-anhydro-2-deoxy-aldono-1,4-
lactones. J. Carbohydr. Chem. 2000, 19(8), 1019–1047.
55. van Delft, F.L.; Valentijn, A.R.P.M.; van der Marel, G.A.; van Boom, J.H. Preparation of 2,5-anhydro
hexitols (Part I). Silicon-directed stereocontrolled cyclization. J. Carbohydr. Chem. 1999, 18(2),
165–190.
56. van Delft, F.L.; Valentijn, A.R.P.; van der Marel, G.A.; van Boom, J.H. Preparation of 2,5-anhydro
hexitols (Part II). Intramolecular nucleophilic substitution of cyclic sulfates. J. Carbohydr. Chem.
1999, 18(2), 191–207.
57. Sharma, G.V.M.; Chander, A.S.; Krishnudu, K.; Krishna, P.R. A simple and efficient PdCl2 mediated
conversion of g,d-olefinic alcohols into C-glycosides. Tetrahedron Lett. 1997, 38(52), 9051–9054.
58. Hiranuma, S.; Shimizu, T.; Nakata, T.; Kajimoto, T.; Wong, C.-H. Synthesis and inhibition analysis of
five-membered homoazasugars from D-arabinofuranose via an SN2 reaction of the chloromethyl-
sulfonate. Tetrahedron Lett. 1995, 36(45), 8247–8250.
59. Kuszmann, J.; Dvortsa´k Synthesis of 6-amino-2,5-anhydro-6-deoxy- and –1,6-dideoxy-D-glucitol and
some derivatives thereof. Carbohydr. Res. 1983, 123(2), 209–229.
60. Stork, G.; Suh, H.S.; Kim, G. The temporary silicon connection method in the control of regio-
and stereochemistry. Applications to radical-mediated reactions. The stereospecific synthesis of
C-glycosides. J. Am. Chem. Soc. 1991, 113(18), 7054–7056.
61. Cornia, M.; Casiraghi, G.; Zetta, L. The diastereoselective arylation of arabinofuranose derivatives
using bromomagnesium phenolates: synthesis of β-D- and α-L-arabinofuranosyl phenols. Tetrahe-
dron 1990, 46(8), 3071–3076.
62. Maryanoff, B.E.; Northey, S.O.; Inners, R.R.; Campbell, A.S.; Reitz, A.B. Synthesis of C-
arabinofuranosyl compounds. Phosphate and carboxylate isosters of D-arabinose 1,5-bis-phosphate.
Carbohydr. Res. 1987, 171, 259–278.
63. Freeman, F.; Robarge, K.D. Stereoselectivity in the electrophile-mediated cyclization of 2,3,5-tri-
O-benzyl-1,2-dideoxy-D-arabino-hex-1-enitol. A stereocontrolled synthesis of 1-amino-2,5-anhydro-
3,4,6-tri-O-benzyl-1-deoxy-D-glucitol. Carbohydr. Res. 1987, 171(1), 1–11.
64. Martin, O.R.; Yang, F.; Xie, F. Spontaneous cyclization of triflates derived from δ-benzyloxy alcohols:
efficient and general synthesis of C-vinyl furanosides. Tetrahedron Lett. 1995, 36(1), 47–50.
65. Persky, R.; Albeck, A. Synthesis of selectively labeled D-fructose and D-fructose phosphate ana-
logues locked in the cyclic furanose form. J. Org. Chem. 2000, 65(18), 5632–5638.
66. Chang, G.X.; Lowary, T.L. An olefin cross metathesis approach to C-disaccharide analogs of the
α-D-arabinofuranosyl-(1→5)-α-D-arabinofuranoside motif found in the mycobacterial cell wall.
Tetrahedron Lett. 2006, 47(27), 4561–4564.
67. Acton, E.M.; Fujiwara, A.N.; Goodman, L.; Henry, D.W. Synthetic C-nucleosides: 3-(α- and β-D-
arabinofuranosyl)pyrazol[4,3-d]pyrimidine-5,7-diones. Carbohydr. Res. 1974, 33(1), 135–151.
68. Jiang, C.; Baur, R.H.; Dechter, J.J.; Baker, D.C. Synthesis and stereochemical assignments for 2-(α-
and β-D-arabinofuranosyl)thiazole-4-carboxamides. Nucleosides Nucleotides 1984, 3(2), 123–146.
69. Pernet, A.G.; Ogawa, T.; Hanessian, S. Synthese, assignation anomerique et epimerization des C-
pentofuranosyle manonates. Tetrahedron Lett. 1975, 37, 3547–3550.
70. Cipolla, L.; Liguori, L.; Nicotra, F.; Torri, G.; Vismara, E. Glycomimetics via a new glycoexoenitols-
malonyl radical C-C bond formation. J. Chem. Soc. Chem. Commun. 1996, 1253–1254.
71. Peri, F.; Bassetti, R.; Caneva, E.; de Gioia, L.; La Ferla, B.; Presta, M.; Tanghetti, E.; Nicotra, F.
Arabinose-derived bicyclic amino acids: synthesis, conformational analysis and construction of an
α β -selective RGD peptide. J. Chem. Soc. Perkin Trans I 2002, 638–644.
v
3
72. O’Leary, D.J.; Kishi, Y. Preferred conformation of C-glycosides. 13. A comparison of the conforma-
tional behavior of several C-, N -, and O-furanosides. J. Org. Chem. 1994, 59(22), 6629–6636.
73. Peri, F.; Airoldi, C.; Colombo, S.; Mari, S.; Jime´nez-Barbero, J.; Martegani, E.; Nicotra, F. Sugar-
derived Ras inhibitors: group epitope mapping by NMR spectroscopy and biological evaluation.
Eur. J. Org. Chem. 2006, 3707–3720.