2-Deoxy-1-thio-a-hexopyranosid-3-ulose
4225
2. (a) Fugedi, P.; Garegg, P. J. A novel promoter for the efficient construction of
1,2-trans linkages in glycoside synthesis, using thioglycosides as glycosyl
donors. Carbohydr. Res. 1986, 149 (1), C9–C12; (b) Mootoo, D. R.;
McDevitt, R. E.; Fraser-Reid, B. Iodonium ion generated in situ from
N-iodosuccinimide and trifluoromethanesulfonic acid promotes direct linkage of
disarmed pent-4-enyl glycosides. J. Chem. Soc., Chem. Commun. 1990, 3,
270–272; (c) Veeneman, G. H.; Van Boom, J. H. Iodonium ion-promoted
reactions at the anomeric center, II: an efficient thioglycoside-mediated
approach toward the formation of 1,2-trans-linked glycosides and glycosidic
esters. Tetrahedron Lett. 1990, 31 (9), 1331–1334; (d) Balavoine, G.;
Berteina, S.; Gref, A.; Fischer, J.-C.; Lubineau, A. Thio glycosides as potential
glycosyl donors in electrochemical glycosidation reactions, part 2: their reactivity
toward sugar alcohols. J. Carbohydr. Chem. 1995, 14 (8), 1237–1249;
(e) Fukase, K.; Kinoshita, I.; Kanoh, T.; Nakai, Y.; Hasuoka, A.; Kusumoto, S.
A
novel method for stereoselective glycosidation with thio glycosides:
promotion by hypervalent iodine reagents prepared from PhIO and various
acids. Tetrahedron 1996, 52 (11), 3897–3904.
3. (a) Kahne, D.; Walker, S.; Chen, Y.; Van Engen, D. Glycosylation of unreactive
substrates. J. Am. Chem. Soc. 1989, 111 (17), 6881–6882; (b) Kim, S. H.;
Augeri, D.; Yang, D.; Kahne, D. Concise synthesis of the calicheamicin oligosac-
charide using the sulfoxide glycosylation method. J. Am. Chem. Soc. 1994, 116 (5),
1766–1775; (c) Yan, L.; Taylor, C. M.; Goodnow, R., Jr.; Kahne, D. Glycosylation
on the merrifield resin using anomeric sulfoxides. J. Am. Chem. Soc. 1994,
116 (15), 6953–6954; (d) Liang, R.; Yan, L.; Loebach, J.; Ge, M.; Uozomi, Y.;
Sekanina, K.; Horan, N.; Gildersleeve, J.; Thompson, C.; Smith, A.; Biswas, K.;
Still, W. C.; Kahne, D. Parallel synthesis and screening of a solid phase carbo-
hydrate library. Science (Washington DC) 1996, 274 (5292), 1520–1522;
(e) Crich, D.; Sun, S. Formation of b-mannopyranosides of primary alcohols
using the sulfoxide method. J. Org. Chem. 1996, 61 (14), 4506–4507;
(f) Sofia, M. J.; Kakarla, R.; Kogan, N.; Dulina, R.; Hui, Y. W.;
Hatzenbuhler, N. T.; Liu, D.; Chen, A.; Wagler, T. The efficient synthesis of a
bis-glycosylated steroid drug transport reagent: methyl 3-b-amino-7a,12-a-
di(10 a-glucosyl)-5b-cholate (TC002). Bioorg. Med. Chem. Lett. 1997, 7 (17),
2251–2254; (g) Barroca, N.; Schmidt, R. 2-Nitro thioglycoside donors: versatile
precursors of b-D-glycosides of aminosugars. Org. Lett. 2004, 6 (10), 1551–1554.
4. (a) Belica, P. S.; Franck, R. W. Benzylic C-glycosides via the Ramberg–Backlund
reaction. Tetrahedron Lett. 1998, 39 (45), 8225–8228; (b) Griffin, F. A.;
Murphy, P. V.; Paterson, D. E.; Taylor, R. J. K. A Ramberg–Backlund
approach to exo-glycals. Tetrahedron Lett. 1998, 39 (44), 8179–8182;
(c) Alcaraz, M.-L.; Griffin, F. A.; Paterson, D. E.; Taylor, R. J. K. Synthetic appli-
cations of Ramberg–Backlund derived exo-glycals. Tetrahedron Lett. 1998,
39 (44), 8183–8186.
5. (a) Chu, S.-H. L.; Anderson, L. Oligosaccharide synthesis by the thioglycoside
scheme on soluble and insoluble polystyrene supports. Carbohydr. Res. 1976,
50 (2), 227–238; (b) Pozsgay, V.; Jennings, H. J. Synthesis of glycosyl esters
and glycosyl hemiacetals from methylthioglycosides. Carbohydr. Chem. 1990,
9 (2–3), 333–343; (c) Lubineau, A.; Auge, J.; Lubin, N. New strategy in the
synthesis of 3-deoxy-D-manno-2-octulosonic acid (KDO), 2-deoxy-KDO and thio-
glycoside of KDO. Tetrahedron 1993, 49 (21), 4639–4650; (d) Motawia, M. S.;
Marcussen, J.; Moeller, B. L. A general method based on the use of N-bromosuc-
cinimide for removal of the thiophenyl group at the anomeric position to generate a