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For reviews:. Morin C. Synthèse de sucres iodés vers l'imagerie SPECT du transport du d-glucose. In: Comet M., and Vidal M. (Eds). Radiopharmaceutiques, chimie des traceurs et applications biologiques (1988), PUG, Grenoble 295-305
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Chem. Abstr. 122 (1995) 260001
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Yamamichi, Y.; Kaji, N.; Fujiwara, M.; Minosako, Y.; Hayashi, A. Jpn. Kokai Tokkyo Koho 1997 0708, 1997; Chem. Abstr. 1997, 127, 173206 and 176656.
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38
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-
49549149007
-
-
2-DIG is also mentioned in Honda, S.; Takiura, K. Carbohydr. Res. 1974, 34, 45-56, but without clear structural support; its preparation could not be reproduced by other workers (see Ref. 12) including ourselves; 2-DIG also lies in two patents (Nakamara, K.; Ono, H.; Ogura, K. Jpn. Kokai Tokkyo Koho 58 069816, 1983; Chem. Abstr. 1985, 99, 27831. Lampidis, T. J.; Priebe, W. WO 082926, 2001; Chem. Abstr. 2001, 135, 339233) but without mention of preparation.
-
-
-
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41
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0036392071
-
-
For recent reviews see inter alia:
-
For recent reviews see inter alia:. Wienhard K. Methods 27 (2002) 218-225
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(2002)
Methods
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-
Wienhard, K.1
-
47
-
-
33744969460
-
-
note
-
As noted in Refs. 4b and 12. This lability could be due to the α-iodo-aldehyde present in the acyclic form.
-
-
-
-
48
-
-
30744473191
-
-
For SOS (Simplicity Oriented Synthesis), see:
-
For SOS (Simplicity Oriented Synthesis), see:. Compain P., Desvergnes V., Ollivier C., Robert F., Suzenet F., Barboiu M., Belmont P., Bleriot Y., Bolze F., Bouquillon S., Bourguet E., Braida B., Constantieux T., Desaubry L., Marat X., Migaud M., Moitessier N., Papot S., Peri F., Petit M., Py S., Schulz E., Tranoy-Opalinski I., Vauzeilles B., Vayron P., Vergnes L., Vidal S., and Wilmouth S. C.R. Chim. 9 (2006) 127-140
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(2006)
C.R. Chim.
, vol.9
, pp. 127-140
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Compain, P.1
Desvergnes, V.2
Ollivier, C.3
Robert, F.4
Suzenet, F.5
Barboiu, M.6
Belmont, P.7
Bleriot, Y.8
Bolze, F.9
Bouquillon, S.10
Bourguet, E.11
Braida, B.12
Constantieux, T.13
Desaubry, L.14
Marat, X.15
Migaud, M.16
Moitessier, N.17
Papot, S.18
Peri, F.19
Petit, M.20
Py, S.21
Schulz, E.22
Tranoy-Opalinski, I.23
Vauzeilles, B.24
Vayron, P.25
Vergnes, L.26
Vidal, S.27
Wilmouth, S.28
more..
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52
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37049089748
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Tailler D., Jacquinet J.-C., Noirot A.-M., and Beau J.-M. J. Chem. Soc., Perkin Trans. 1 (1992) 3163-3164
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(1992)
J. Chem. Soc., Perkin Trans. 1
, pp. 3163-3164
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Tailler, D.1
Jacquinet, J.-C.2
Noirot, A.-M.3
Beau, J.-M.4
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57
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1842684023
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Barluenga J., Marco-Arias M., Gonzales-Bobes F., Ballesteros A., and Gonzales J.M. Chem. Eur. J. 10 (2004) 1677-1682
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Barluenga, J.1
Marco-Arias, M.2
Gonzales-Bobes, F.3
Ballesteros, A.4
Gonzales, J.M.5
-
58
-
-
33744983440
-
-
note
-
3,4 = 9 Hz).
-
-
-
-
59
-
-
0027109452
-
-
13C NMR data of α-5, see:
-
13C NMR data of α-5, see:. Miljkovic D., Djurendic E., Vukojevic N., Gasi K., and Csanadi J. Carbohydr. Res. 233 (1992) 251-253
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Carbohydr. Res.
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Miljkovic, D.1
Djurendic, E.2
Vukojevic, N.3
Gasi, K.4
Csanadi, J.5
-
62
-
-
0032366177
-
-
3): 90.4 (C-1); 74.2, 71.8, 67.3 (C-3, C-4, C-5) 62.6 (C-6), 32.5 (C-2)
-
3): 90.4 (C-1); 74.2, 71.8, 67.3 (C-3, C-4, C-5) 62.6 (C-6), 32.5 (C-2)
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(1998)
J. Serb. Chem. Soc.
, vol.63
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Djurendic, E.1
Vukovecik, N.2
Drammicanin, T.3
Canadi, J.4
Milkovic, D.5
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66
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9644295926
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Gammon D.W., Kinfe H.H., De Vos D.E., Jacobs P.A., and Sels B.F. Tetrahedron Lett. 45 (2004) 9533-9536
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Gammon, D.W.1
Kinfe, H.H.2
De Vos, D.E.3
Jacobs, P.A.4
Sels, B.F.5
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69
-
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33744983225
-
-
note
-
We have found that the intermediate persilylated 1-O-acetyl-2-deoxy-2-iodo gluco isomer can be easily freed from the (minor) manno isomer by fractional crystallization from n-hexane. Also, after the silyl ethers deprotection step (Ref. 27) mere washing of the crude organic residue with ether/pentane (1:1) results in pure crystalline 8.
-
-
-
-
70
-
-
49549143786
-
-
This reagent is usually used for selective deacylation of anomeric acetates in peracetylated carbohydrates: ; in 8, as a single acetate is to be removed, DMF can advantageously be replaced by methanol, which facilitates isolation of 1
-
This reagent is usually used for selective deacylation of anomeric acetates in peracetylated carbohydrates:. Excoffier G., Gagnaire D., and Utille J.-P. Carbohydr. Res. 39 (1975) 368-373 ; in 8, as a single acetate is to be removed, DMF can advantageously be replaced by methanol, which facilitates isolation of 1
-
(1975)
Carbohydr. Res.
, vol.39
, pp. 368-373
-
-
Excoffier, G.1
Gagnaire, D.2
Utille, J.-P.3
-
71
-
-
33744985173
-
-
note
-
2O): 97.0 (C-1β), 93.8 (C-1α), 77.5, 76.4, 70.7 (C-3β, C-4β, C-5β), 73.8, 72.4, C-3α, C-4α, C-5α), 61.0 (C-6β), 60.9 (C-6α)t, 36.9 (C-2β), 33.4 (C-2α).
-
-
-
-
72
-
-
0343802676
-
-
3): 92.1 (C-1), 77.6, 72.8, 70.4 (C-3, C-4, C-5), 61.9 (C-6), 23.7 (C-2).
-
3): 92.1 (C-1), 77.6, 72.8, 70.4 (C-3, C-4, C-5), 61.9 (C-6), 23.7 (C-2).
-
(1987)
J. Carbohydr. Chem.
, vol.6
, pp. 203-219
-
-
Binkley, R.W.1
Ambrose, M.G.2
Hehemann, D.G.3
-
73
-
-
33745005184
-
-
note
-
Being an iodinated compound, 1 should be protected from strong light however.
-
-
-
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