-
1
-
-
0000748301
-
-
A. Dondoni, A. Marra, P. Merino, J. Am. Chem. Soc. 1994, 116, 3324-3336.
-
(1994)
J. Am. Chem. Soc.
, vol.116
, pp. 3324-3336
-
-
Dondoni, A.1
Marra, A.2
Merino, P.3
-
2
-
-
0025818102
-
-
For an alternative route via aldol condensation of the lithium enolate of 2-acetylthiazole as an equivalent of the pyruvate anion, see: A. Dondoni, P. Merino, J. Org. Chem. 1991, 56, 5294-5301. The same synthetic approach has been recently extended by others to the preparation of analogues of Neu5Ac [ref. 7f] while the relevant reference to the our earlier work was omitted.
-
(1991)
J. Org. Chem.
, vol.56
, pp. 5294-5301
-
-
Dondoni, A.1
Merino, P.2
-
3
-
-
0022978138
-
-
D. Nadano, M. Iwasaki, S. Endo, K. Kitajima, S. Inoue, Y. Inoue, J. Biol. Chem. 1986, 261, 11550-11557.
-
(1986)
J. Biol. Chem.
, vol.261
, pp. 11550-11557
-
-
Nadano, D.1
Iwasaki, M.2
Endo, S.3
Kitajima, K.4
Inoue, S.5
Inoue, Y.6
-
4
-
-
0001276617
-
Sialic acids. Chemistry, metabolism, and function
-
Springer Verlag, Wien
-
Sialic Acids. Chemistry, Metabolism, and Function in Cell Biology Monographs (Ed.: R. Schauer), Springer Verlag, Wien, 1982.
-
(1982)
Cell Biology Monographs
-
-
Schauer, R.1
-
6
-
-
0026445723
-
-
For recent reviews on the biological roles of sialic acids, see: a) L. A. Lasky, Science 1992, 258, 964-969;
-
(1992)
Science
, vol.258
, pp. 964-969
-
-
Lasky, L.A.1
-
9
-
-
0000525695
-
-
d) A. Giannis, Angew. Chem. 1994, 106, 188-191; Angew. Chem. Int. Ed. Engl. 1994, 33, 178-180;
-
(1994)
Angew. Chem.
, vol.106
, pp. 188-191
-
-
Giannis, A.1
-
10
-
-
0028121730
-
-
d) A. Giannis, Angew. Chem. 1994, 106, 188-191; Angew. Chem. Int. Ed. Engl. 1994, 33, 178-180;
-
(1994)
Angew. Chem. Int. Ed. Engl.
, vol.33
, pp. 178-180
-
-
-
12
-
-
0001094662
-
-
f) R. A. Dwek, Chem. Rev. 1996, 96, 683-720.
-
(1996)
Chem. Rev.
, vol.96
, pp. 683-720
-
-
Dwek, R.A.1
-
13
-
-
37049080529
-
-
For recent papers with leading references, see: a) M. J. Bamford, J. C. Pichel, W. Husman, B. Patel, R. Storer, N. G. Weir, J. Chem. Soc. Perkin Trans 1 1995, 1181-1187;
-
(1995)
J. Chem. Soc. Perkin Trans 1
, pp. 1181-1187
-
-
Bamford, M.J.1
Pichel, J.C.2
Husman, W.3
Patel, B.4
Storer, R.5
Weir, N.G.6
-
14
-
-
0028783528
-
-
b) B. P. Bandgar, S. V. Patil, E. Zbiral, Carbohydr. Res. 1995, 276, 337-345;
-
(1995)
Carbohydr. Res.
, vol.276
, pp. 337-345
-
-
Bandgar, B.P.1
Patil, S.V.2
Zbiral, E.3
-
16
-
-
0031048243
-
-
d) X.-L. Sun, T. Kai, H. Takayanagi, K. Furuhata, Carbohydr. Res. 1997, 298, 181 -189;
-
(1997)
Carbohydr. Res.
, vol.298
, pp. 181-189
-
-
Sun, X.-L.1
Kai, T.2
Takayanagi, H.3
Furuhata, K.4
-
18
-
-
0032554490
-
-
f) M. Banwell, C. De Savi, D. Hockless, K. Watson, Chem. Commun. 1998, 645-646.
-
(1998)
Chem. Commun.
, pp. 645-646
-
-
Banwell, M.1
De Savi, C.2
Hockless, D.3
Watson, K.4
-
19
-
-
0027082554
-
-
The synthesis of 5-acetamidomethyl-3,5-dideoxy-nonulosonic acid derivative, a homologue of Neu5Ac (1), has been reported: K. Koppert, R. Brossmer, Tetrahedron Lett. 1992, 33, 8031-8034.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 8031-8034
-
-
Koppert, K.1
Brossmer, R.2
-
20
-
-
0000144488
-
-
Amines, selected references, see: a) H. Matsunaga, T. Sakamaki, N. Nagaoka, Y. Yamada, Tetrahedron Lett. 1983, 24, 3009-3012;
-
(1983)
Tetrahedron Lett.
, vol.24
, pp. 3009-3012
-
-
Matsunaga, H.1
Sakamaki, T.2
Nagaoka, N.3
Yamada, Y.4
-
22
-
-
0000734905
-
-
c) B. de Lange, F. van Bolhuis, B. L. Feringa, Tetrahedron 1989, 45, 6799-6818;
-
(1989)
Tetrahedron
, vol.45
, pp. 6799-6818
-
-
De Lange, B.1
Van Bolhuis, F.2
Feringa, B.L.3
-
23
-
-
0024998611
-
-
d) A. Dondoni, G. Fantin, M. Fogagnolo, P. Merino, Tetrahedron 1990, 46, 6167-6184;
-
(1990)
Tetrahedron
, vol.46
, pp. 6167-6184
-
-
Dondoni, A.1
Fantin, G.2
Fogagnolo, M.3
Merino, P.4
-
24
-
-
0029055876
-
-
e) C. J. Andres, P. H. Lee, T. H. Nguyen, A. I. Meyers, J. Org. Chem. 1995, 60, 3189-3193;
-
(1995)
J. Org. Chem.
, vol.60
, pp. 3189-3193
-
-
Andres, C.J.1
Lee, P.H.2
Nguyen, T.H.3
Meyers, A.I.4
-
26
-
-
0029023947
-
-
g) M. P. Collis, D. C. R. Hockless, P. Perlmutter, Tetrahedron Lett. 1995, 36, 7133-7136.
-
(1995)
Tetrahedron Lett.
, vol.36
, pp. 7133-7136
-
-
Collis, M.P.1
Hockless, D.C.R.2
Perlmutter, P.3
-
27
-
-
0042960761
-
-
Metal amides, selected references, see: a) J. M. Hawkins, G. C. Fu, J. Org. Chem. 1986, 51, 2820-2822;
-
(1986)
J. Org. Chem.
, vol.51
, pp. 2820-2822
-
-
Hawkins, J.M.1
Fu, G.C.2
-
29
-
-
0000161396
-
-
c) N. Asao, T. Uyehara, Y. Yamamoto, Tetrahedron 1990, 46, 4563-4577;
-
(1990)
Tetrahedron
, vol.46
, pp. 4563-4577
-
-
Asao, N.1
Uyehara, T.2
Yamamoto, Y.3
-
32
-
-
0026628984
-
-
f) Y. Yamamoto, N. Asao, T. Uyehara, J. Am. Chem. Soc. 1992, 114, 5427-5429;
-
(1992)
J. Am. Chem. Soc.
, vol.114
, pp. 5427-5429
-
-
Yamamoto, Y.1
Asao, N.2
Uyehara, T.3
-
34
-
-
0028808860
-
-
h) N. Tsukada, T. Shimada, Y. S. Gyoung, N. Asao, Y. Yamamoto, J. Org. Chem. 1995, 60, 143-148;
-
(1995)
J. Org. Chem.
, vol.60
, pp. 143-148
-
-
Tsukada, N.1
Shimada, T.2
Gyoung, Y.S.3
Asao, N.4
Yamamoto, Y.5
-
35
-
-
0000891278
-
-
i) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 455-457;
-
(1995)
Angew. Chem.
, vol.107
, pp. 527-529
-
-
Enders, D.1
Wahl, H.2
Bettray, W.3
-
36
-
-
33748232894
-
-
i) D. Enders, H. Wahl, W. Bettray, Angew. Chem. 1995, 107, 527-529; Angew. Chem. Int. Ed. Engl. 1995, 34, 455-457;
-
(1995)
Angew. Chem. Int. Ed. Engl.
, vol.34
, pp. 455-457
-
-
-
37
-
-
0001325824
-
-
j) N. Asao, T. Shimada, T. Sudo, N. Tsukada, K. Yazawa, Y. S. Gyoung, T. Uyehara, Y. Yamamoto, J. Org. Chem. 1997, 62, 6274-6282.
-
(1997)
J. Org. Chem.
, vol.62
, pp. 6274-6282
-
-
Asao, N.1
Shimada, T.2
Sudo, T.3
Tsukada, N.4
Yazawa, K.5
Gyoung, Y.S.6
Uyehara, T.7
Yamamoto, Y.8
-
38
-
-
85050326125
-
Stereochemistry of the base-promoted Michael addition reactions
-
(Eds.: E. L. Eliel, S. H. Wilen), Wiley, New York
-
Monographs; a) D. A. Oare, C. H. Heathcock, Stereochemistry of the Base-Promoted Michael Addition Reactions in Topics in Stereo-chemistry (Eds.: E. L. Eliel, S. H. Wilen), Wiley, New York, 1989, pp. 227-407;
-
(1989)
Topics in Stereo-chemistry
, pp. 227-407
-
-
Oare, D.A.1
Heathcock, C.H.2
-
40
-
-
0003280270
-
Conjugate addition reactions in organic synthesis
-
(Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford
-
c) P. Perlmutter, Conjugate Addition Reactions in Organic Synthesis, In Tetrahedron Organic Chemistry Series, Vol. 9 (Eds.: J. E. Baldwin, P. D. Magnus), Pergamon, Oxford, 1992;
-
(1992)
Tetrahedron Organic Chemistry Series
, vol.9
-
-
Perlmutter, P.1
-
43
-
-
85088281338
-
-
note
-
2). At - 70°C the reaction proceeded with a good level of selectivity (ca. 9:1) up to completion but the product ratio changed to a constant 1:1 value on standing at room temperature for 16 hours.
-
-
-
-
44
-
-
0348249080
-
-
note
-
In general the NMR spectra at room temperature of compounds containing an N,N-dialkyl-N-Boc amine function show a double set of signals arising from the hindered rotation around the σ-bonds. Hence the spectrum of a mixture of epimers can be rather complex due to the presence of the corresponding rotamers. At higher temperatures (120-160°C) the spectra become simpler because of the coalescence of signals.
-
-
-
-
45
-
-
0346988319
-
-
note
-
The α-D anomeric configuration of 9a and 13, and the β-D configuration of 9b were supported by a substantial NOE between the methoxy group and H-5ax.
-
-
-
-
46
-
-
0032447309
-
-
For a recent account on methods and synthetic applications based on the thiazole-aldehyde equivalence, see: A. Dondoni, Synthesis 1998, 1681-1706.
-
(1998)
Synthesis
, pp. 1681-1706
-
-
Dondoni, A.1
-
47
-
-
33751386554
-
-
A. Dondoni, A. Marra, D. Perrone, J. Org. Chem. 1993, 58, 275-277.
-
(1993)
J. Org. Chem.
, vol.58
, pp. 275-277
-
-
Dondoni, A.1
Marra, A.2
Perrone, D.3
-
48
-
-
0348249079
-
-
note
-
It is worth recalling here that the direct conversion of the thiazole ring into the carboxylate group has been found so far to be unpractical as a result of low yields and harsh conditions, see [ret. 1].
-
-
-
-
49
-
-
0346988318
-
-
note
-
This N-protective group arrangement was proved to be crucial in various thiazole-based syntheses, see [ref. 5].
-
-
-
-
50
-
-
0001795660
-
-
Various transition state models, some of which empirical [ref. 11a], other based on molecular mechanics: A. Bernardi, A. M. Capelli, C. Gennari, C. Scolastico, Tetrahedron: Asymmetry 1990, 1, 21-32 and molecular orbital studies: A. E. Dorigo, K. Morokuma, J. Am. Chem. Soc. 1989, 111, 6524-6536 have been proposed to account for the variable stereochemical outcome of Michael-type reactions.
-
(1990)
Tetrahedron: Asymmetry
, vol.1
, pp. 21-32
-
-
Bernardi, A.1
Capelli, A.M.2
Gennari, C.3
Scolastico, C.4
-
51
-
-
0000449145
-
-
Various transition state models, some of which empirical [ref. 11a], other based on molecular mechanics: A. Bernardi, A. M. Capelli, C. Gennari, C. Scolastico, Tetrahedron: Asymmetry 1990, 1, 21-32 and molecular orbital studies: A. E. Dorigo, K. Morokuma, J. Am. Chem. Soc. 1989, 111, 6524-6536 have been proposed to account for the variable stereochemical outcome of Michael-type reactions.
-
(1989)
J. Am. Chem. Soc.
, vol.111
, pp. 6524-6536
-
-
Dorigo, A.E.1
Morokuma, K.2
-
52
-
-
0027972107
-
-
For a preliminary report of this synthesis, see: A. Dondoni, A. Boscarato, A. Marra, Tetrahedron: Asymmetry 1994, 5, 2209-2212.
-
(1994)
Tetrahedron: Asymmetry
, vol.5
, pp. 2209-2212
-
-
Dondoni, A.1
Boscarato, A.2
Marra, A.3
-
54
-
-
0032514526
-
-
b) A. Dondoni, S. Daninos, A. Marra, P. Formaglio Tetrahedron 1998, 54, 9859-9874.
-
(1998)
Tetrahedron
, vol.54
, pp. 9859-9874
-
-
Dondoni, A.1
Daninos, S.2
Marra, A.3
Formaglio, P.4
-
55
-
-
0346988317
-
-
note
-
Compound 3 was contaminated by ca. 10% of unreacted Me-3 which could not be removed by chromatography. An alternative synthesis of this compound has been recently reported by others [ref. 7e].
-
-
-
-
56
-
-
85088280363
-
-
note
-
3 to 5 and 6 were essentially unselective.
-
-
-
-
57
-
-
0001339951
-
-
a) A. Ricci, A. Degl' Innocenti, G. Borselli, G. Reginato, Tetrahedron Lett. 1987, 28, 4093-4096;
-
(1987)
Tetrahedron Lett.
, vol.28
, pp. 4093-4096
-
-
Ricci, A.1
Degl' Innocenti, A.2
Borselli, G.3
Reginato, G.4
-
58
-
-
0001170074
-
-
b) M. Ochiai, M. Kunishima, K. Fuji, Y. Nagao, J. Org. Chem. 1988, 53, 6144-6145;
-
(1988)
J. Org. Chem.
, vol.53
, pp. 6144-6145
-
-
Ochiai, M.1
Kunishima, M.2
Fuji, K.3
Nagao, Y.4
-
59
-
-
0026524145
-
-
c) A. Degl' Innocenti, A. Capperucci, G. Reginato, A. Mordini, A. Ricci, Tetrahedron Lett. 1992, 33, 1507-1508.
-
(1992)
Tetrahedron Lett.
, vol.33
, pp. 1507-1508
-
-
Degl' Innocenti, A.1
Capperucci, A.2
Reginato, G.3
Mordini, A.4
Ricci, A.5
-
61
-
-
0027366768
-
-
b) J. S. Plummer, L. A. Emery, M. A. Stier, M. J. Suto, Tetrahedron Lett. 1993, 34, 7529-7532;
-
(1993)
Tetrahedron Lett.
, vol.34
, pp. 7529-7532
-
-
Plummer, J.S.1
Emery, L.A.2
Stier, M.A.3
Suto, M.J.4
-
63
-
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0346988316
-
-
note
-
The anomeric configuration was proved by NOE experiments.
-
-
-
-
64
-
-
0347583459
-
-
note
-
The incorporation of protective groups under basic conditions was not compatible with the nitromethyl group. Benzylation under acidic conditions and acetonation was unsuccessful.
-
-
-
-
65
-
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0028834594
-
-
Very likely the N-methylation of the thiazole ring was accompanied by the formation of an unstable methyl imidate function from the acetamido group at C-4. On the other hand the thiazole-to-formyl deblocking protocol is fully compatible with the presence of a NHBoc group, see [ref. 16] and A. Dondoni, D. Perrone, P. Merino, J. Org. Chem. 1995, 60, 8074-8080.
-
(1995)
J. Org. Chem.
, vol.60
, pp. 8074-8080
-
-
Dondoni, A.1
Perrone, D.2
Merino, P.3
-
66
-
-
0004055425
-
-
Butterworth-Heinemann, Oxford
-
W. L. F. Armarego, D. D. Perrin, Purification of Laboratory Chemicals, 4th ed., Butterworth-Heinemann, Oxford, 1996.
-
(1996)
Purification of Laboratory Chemicals, 4th Ed.
-
-
Armarego, W.L.F.1
Perrin, D.D.2
-
67
-
-
0002714675
-
-
W. C. Still, M. Kahn, A. Mitra, J. Org. Chem. 1978, 43, 2923-2925.
-
(1978)
J. Org. Chem.
, vol.43
, pp. 2923-2925
-
-
Still, W.C.1
Kahn, M.2
Mitra, A.3
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