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1
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0024209272
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Two reviews dealing with various aspects of nucleoside antibiotic chemistry have recently been published
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K. J. Antibiotics
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Two reviews dealing with various aspects of nucleoside antibiotic chemistry have recently been published: (a) Structure, Biological Activity, and Biosynthesis: Isono, K. J. Antibiotics 1988, 41, 1711.
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(1988)
Structure, Biological Activity, and Biosynthesis: Isono
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2
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0003373977
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Synthetic Approaches to Complex Nucleoside Antibiotics
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Stereoselective Synthesis, Part A; Atta-Ur-Rahman, E.; Elsevier: Amsterdam
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Garner, P. Synthetic Approaches to Complex Nucleoside Antibiotics. In Studies in Natural Products Chemistry, Vol. 1. Stereoselective Synthesis, Part A; Atta-Ur-Rahman, E.; Elsevier: Amsterdam, 1988; pp 397–434.
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(1988)
Studies in Natural Products Chemistry
, vol.1
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Garner, P.1
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3
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0014682610
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Isono, K.; Asahi, K.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7490.
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J. Am. Chem. Soc.
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Isono, K.1
Asahi, K.2
Suzuki, S.3
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4
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85022880274
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For a comprehensive review of the polyoxins
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For a comprehensive review of the polyoxins, see: Isono, K.; Suzuki, S. Heterocycles 1979, 13, 333.
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(1979)
Heterocycles
, vol.13
, Issue.333
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Isono, K.1
Suzuki, S.2
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5
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0019948905
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Goto, T.; Toya, Y.; Ohgi, T.; Kondto, T. Tetrahedron Lett. 1982, 1271.
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(1982)
Tetrahedron Lett.
, pp. 1271
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Goto, T.1
Toya, Y.2
Ohgi, T.3
Kondto, T.4
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8
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85022901571
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Tabusa, F.; Yamada, T.; Suzuki, K.; Mukaiyama, T. Chem. Lett. 1984, 405.
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Chem. Lett.
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Tabusa, F.1
Yamada, T.2
Suzuki, K.3
Mukaiyama, T.4
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9
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0001078307
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Mukaiyama, T.; Suzuki, K.; Yamada, T.; Tabusa, F. Tetrahedron 1990, 46, 265.
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(1990)
Tetrahedron
, vol.46
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Mukaiyama, T.1
Suzuki, K.2
Yamada, T.3
Tabusa, F.4
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10
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0000594151
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Using Strecker methodology
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Using Strecker methodology: (e) Damodaran, N. P.; Jones, G. H.; Moffatt, J. G. J. Am. Chem. Soc. 1971, 93, 3812.
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(1971)
J. Am. Chem. Soc.
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Damodaran, N.P.1
Jones, G.H.2
Moffatt, J.G.3
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13
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85081228570
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Fiandor, J.; Garcia-Lopez, M.-T.; De las Heras, F. G.; Mendez-Castrillon, P. P. Synthesis 1987, 978.
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(1987)
Synthesis
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Fiandor, J.1
Garcia-Lopez, M.-T.2
De las Heras, F.G.3
Mendez-Castrillon, P.P.4
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14
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0018903926
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Via the Ugi 4-component condensation
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Via the Ugi 4-component condensation: (i) Joullie, M. M.; Wang, P. C.; Semple, J. E. J. Am. Chem. Soc. 1980, 102, 887.
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J. Am. Chem. Soc.
, vol.102
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Joullie, M.M.1
Wang, P.C.2
Semple, J.E.3
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15
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0019186783
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Semple, J. E.; Wang, P. C.; Lysenko, Z.; Joullie, M. M. J. Am. Chem. Soc. 1980, 102, 7505.
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J. Am. Chem. Soc.
, vol.102
, pp. 7505
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Semple, J.E.1
Wang, P.C.2
Lysenko, Z.3
Joullie, M.M.4
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16
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0019268148
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Tsuchida, K.; Mizuno, Y.; Ikeda, K. Nucleic Acids Symp. Series 1980, 8, s49.
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(1980)
Nucleic Acids Symp. Series
, vol.8
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Tsuchida, K.1
Mizuno, Y.2
Ikeda, K.3
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17
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85022854212
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By reduction of a-oximinoesters
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By reduction of a-oximinoesters: (1) Masamune, T.; Ono, M. Chem. Lett. 1975, 625.
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(1975)
Chem. Lett.
, vol.625
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Masamune, T.1
Ono, M.2
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18
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37049122324
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By hydrogenation of a,0-unsaturated a-amino acids
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By hydrogenation of a,0-unsaturated a-amino acids: (m) Bischofberger, K.; Hall, R. H.; Jordaan, A. J. Chem. Soc. Chem. Commun. 1975, 806.
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(1975)
J. Chem. Soc. Chem. Commun.
, vol.806
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Bischofberger, K.1
Hall, R.H.2
Jordaan, A.3
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26
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0023829981
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Other synthetic applications of 4 and its antipode include the following. The sphingosine bases
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Other synthetic applications of 4 and its antipode include the following. The sphingosine bases: (a) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Medici, A. J. Chem. Soc., Chem. Commun. 1988, 10.
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(1988)
J. Chem. Soc., Chem. Commun.
, vol.10
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Dondoni, A.1
Fantin, G.2
Fogagnolo, M.3
Medici, A.4
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28
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0023904902
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Nimkar, S.; Menaldino, D.; Merrill, A. H.; Liotta, D. Tetrahedron Lett. 1988, 3037.
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(1988)
Tetrahedron Lett.
, pp. 3037
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Nimkar, S.1
Menaldino, D.2
Merrill, A.H.3
Liotta, D.4
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29
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0023684709
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Garner, P.; Park, J. M.; Malecki, E. J. Org. Chem. 1988, 53, 4395.
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(1988)
J. Org. Chem.
, vol.53
, pp. 4395
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Garner, P.1
Park, J.M.2
Malecki, E.3
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32
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0003020662
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Prepared in two steps (37% overall distilled yield on a 5-mol scale) from acrolein by a route analogous to that reported for propiolaldehyde diethyl acetal
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Coates, R. M., E.; Wiley: New York
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Prepared in two steps (37% overall distilled yield on a 5-mol scale) from acrolein by a route analogous to that reported for propiolaldehyde diethyl acetal: Le Coq, A.; Gorgues, A. In Organic Syntheses; Coates, R. M., E.; Wiley: New York, 1979; Vol. 59, pp 10–15.
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(1979)
Organic Syntheses
, vol.59
, pp. 10-15
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Le Coq, A.1
Gorgues, A.2
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33
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0342587613
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However, we found it more convenient and economical to use KOH as the base for the double dehydrohalogenation step rather than the 300 mol % of Bu4N+HSO4’ reported in the Organic Syntheses procedure
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However, we found it more convenient and economical to use KOH as the base for the double dehydrohalogenation step rather than the 300 mol % of Bu4N+HSO4’ reported in the Organic Syntheses procedure. Cf.: Sheehan, J. C.; Robinson, C. A. J. Am. Chem. Soc. 1949, 71, 1436.
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(1949)
J. Am. Chem. Soc.
, vol.71
, pp. 1436
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Sheehan, J.C.1
Robinson, C.A.2
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35
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85022805291
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Anh, N. T.; Eisenstein, O. Nouv, J. Chem. 1977, 1, 61.
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(1977)
Nouv, J. Chem.
, vol.1
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Anh, N.T.1
Eisenstein, O.2
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39
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85022784371
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Chemical evidence for the Z-olefin geometry in 10 was gleaned at this stage from an attempted high temperature 13C NMR experiment wherein it was observed that prolonged heating of a C6D6 solution of 10 at 60 °C for a period of 4–5 h resulted in spontaneous cyclization to the dihydrofurans 11 and 12. Cf
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Chemical evidence for the Z-olefin geometry in 10 was gleaned at this stage from an attempted high temperature 13C NMR experiment wherein it was observed that prolonged heating of a C6D6 solution of 10 at 60 °C for a period of 4–5 h resulted in spontaneous cyclization to the dihydrofurans 11 and 12. Cf.: Seyfath, H. E. Chem. Ber. 1968, 101, 619.
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(1968)
Chem. Ber.
, vol.101
, Issue.619
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Seyfath, H.E.1
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40
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33744586503
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Miyashita, M.; Yoshikoshi, A.; Grieco, P. A. J. Org. Chem. 1977, 42, 3772.
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(1977)
J. Org. Chem.
, vol.42
, pp. 3772
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Miyashita, M.1
Yoshikoshi, A.2
Grieco, P.A.3
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42
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33748632563
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and references cited therein
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Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron 1984, 40, 2247 and references cited therein.
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(1984)
Tetrahedron
, vol.40
, pp. 2247
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Cha, J.K.1
Christ, W.J.2
Kishi, Y.3
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44
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0000290377
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The 13C chemical shift of the anomeric carbons in these compounds was, however, indicative of the spacial relationship between the substituents at C-4’ and C-5’ with the respective anomeric carbons of 15 and 16 (both 4‘,5’-trans disubstituted) resonating 7.8 and 5.6 ppm downfield of the anomeric carbon in 17 (4/,5/-cis disubstituted). Cf
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The 13C chemical shift of the anomeric carbons in these compounds was, however, indicative of the spacial relationship between the substituents at C-4’ and C-5’ with the respective anomeric carbons of 15 and 16 (both 4‘,5’-trans disubstituted) resonating 7.8 and 5.6 ppm downfield of the anomeric carbon in 17 (4/,5/-cis disubstituted). Cf.: Ritchie, R. G. S.; Cyr, N.; Korsch, B.; Koch, H. J.; Perlin, A. S. Can. J. Chem. 1975, 53, 1424.
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(1975)
Can. J. Chem.
, vol.53
, pp. 1424
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Ritchie, R. G. S.1
Cyr, N.2
Korsch, B.3
Koch, H.J.4
Perlin, A.S.5
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45
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34547130099
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For a review of the use of carbon-13 NMR spectroscopy for structural characterization of monosaccharides
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For a review of the use of carbon-13 NMR spectroscopy for structural characterization of monosaccharides, see: Bock, K.; Pedersen, C. Adv. Carbohydr. Chem. Biochem. 1983, 41, 27.
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(1983)
Adv. Carbohydr. Chem. Biochem.
, vol.41
, Issue.27
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Bock, K.1
Pedersen, C.2
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46
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2542433188
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We did not experience any difficulty with this oxidation, performed here in aqueous acetone, due to the formation of (inactive) lower valent ruthenium carboxylates. Compare
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We did not experience any difficulty with this oxidation, performed here in aqueous acetone, due to the formation of (inactive) lower valent ruthenium carboxylates. Compare: Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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(1981)
J. Org. Chem.
, vol.46
, pp. 3936
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Carlsen, P. H. J.1
Katsuki, T.2
Martin, V.S.3
Sharpless, K.B.4
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47
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0001690117
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Prepared by mild esterification of 38 using amberlyst-15 as an acid catalyst
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followed by standard O-acetylation (Ac20 + Pyridine)
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Prepared by mild esterification of 38 using amberlyst-15 as an acid catalyst (Petrini, M.; Ballini, R.; Marcantoni, E.; Rosini, G. Synth. Commun. 1988, 18, 847) followed by standard O-acetylation (Ac20 + Pyridine).
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(1988)
Synth. Commun.
, vol.18
, Issue.847
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Petrini, M.1
Ballini, R.2
Marcantoni, E.3
Rosini, G.4
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49
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84982068675
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TMSOTf catalysis
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TMSOTf catalysis: Vorbruggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
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(1981)
Chem. Ber.
, vol.114
, pp. 1234
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Vorbruggen, H.1
Krolikiewicz, K.2
Bennua, B.3
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52
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85022791295
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Preliminary indication that the benzyloxycarbonyl group would survive these acidic nucleosidation conditions was available to us
-
Preliminary indication that the benzyloxycarbonyl group would survive these acidic nucleosidation conditions was available to us. See: Paulsen, H.; Brieden, M.; Benz, G. Justus Leibigs Ann. Chem. 1987, 565.
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(1987)
Justus Leibigs Ann. Chem.
, vol.565
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Paulsen, H.1
Brieden, M.2
Benz, G.3
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53
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33947472819
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Acyclic nucleosides such as this are not unknown. See for example
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Acyclic nucleosides such as this are not unknown. See for example: Wolfrom, M. L.; Foster, A. B.; McWain, P.; Bebenburg, W. v.; Thompson, A. J. Org. Chem. 1961, 26, 3095.
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(1961)
J. Org. Chem.
, vol.26
, pp. 3095
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Wolfrom, M.L.1
Foster, A.B.2
McWain, P.3
Bebenburg, W.v.4
Thompson, A.5
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54
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0001048426
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The question of just what factors govern endocyclic versus exocyclic glycosyl cleavage in sugars is of general interest, but a detailed understanding of the problem remains somewhat elusive
-
The question of just what factors govern endocyclic versus exocyclic glycosyl cleavage in sugars is of general interest, but a detailed understanding of the problem remains somewhat elusive. (Of.: Cosse-Barbi, A.; Watson, D. G.; Dubois, J. E. Tetrahedron Lett. 1989, 163.
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(1989)
Tetrahedron Lett.
, vol.163
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Cosse-Barbi, A.1
Watson, D.G.2
Dubois, J.E.3
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57
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0002085548
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Midland, M. M.; Tramontano, A.; Cable, J. R. J. Org. Chem. 1980, 45, 28.
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J. Org. Chem.
, vol.45
, Issue.28
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Midland, M.M.1
Tramontano, A.2
Cable, J.R.3
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58
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0010640653
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Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
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J. Org. Chem.
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Dale, J.A.1
Dull, D.L.2
Mosher, H.S.3
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59
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0018352995
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Hermann, J. L.; Berger, M. H.; Schlessinger, R. H. J. Am. Chem. Soc. 1979, 101, 1544.
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J. Am. Chem. Soc.
, vol.101
, pp. 1544
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Hermann, J.L.1
Berger, M.H.2
Schlessinger, R.H.3
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61
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0000278459
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We thank Professor Frank Hauser (SUNY/Albany) for alerting us to the advantages of substituting trimethylamine-N-oxide as the carrier oxidant in this reaction
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We thank Professor Frank Hauser (SUNY/Albany) for alerting us to the advantages of substituting trimethylamine-N-oxide as the carrier oxidant in this reaction. Cf. Ray, R.; Matteson, D. S. Tetrahedron Lett. 1980, 449.
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(1980)
Tetrahedron Lett.
, vol.449
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Ray, R.1
Matteson, D.S.2
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64
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85022812123
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Lukes, R.; Moll, M.; Zobacova, A.; Jary, J. Collect. Czech. Commun. 1962, 27, 500.
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(1962)
Collect. Czech. Commun.
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Lukes, R.1
Moll, M.2
Zobacova, A.3
Jary, J.4
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65
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85022799443
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A similar problem was encountered by Rosenthal and Cliff d their work on the synthesis of polyoxin analogues having the 1 fluoroacetamido glycine methyl ester moiety appended to C-3
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A similar problem was encountered by Rosenthal and Cliff d their work on the synthesis of polyoxin analogues having the 1 fluoroacetamido glycine methyl ester moiety appended to C-3, see: senthal, A.; Cliff, B. Carbohydr. Res. 1980, 79, 63.
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Carbohydr. Res.
, vol.79
, Issue.63
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senthal, A.1
Cliff, B.2
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66
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85022843301
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The numbering system used in this paper corresponds to the current CA index names for substructures i—iii. For details
-
American Chemical Society: Washington, DC
-
The numbering system used in this paper corresponds to the current CA index names for substructures i—iii. For details, see: Chemical Abstracts Service Index Guide; American Chemical Society: Washington, DC, 1989.
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(1989)
Chemical Abstracts Service Index Guide
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67
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85022768070
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For more information about the “attached proton test” (APT)
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Advanced Operation; Publication No. 87-146-006, Rev. A383; Varian Instrument Division: Palo Alto, CA
-
For more information about the “attached proton test” (APT), see: XL-Series NMR Spectrometer System. Advanced Operation; Publication No. 87-146-006, Rev. A383; Varian Instrument Division: Palo Alto, CA, 1983; pp 2–29.
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(1983)
XL-Series NMR Spectrometer System
, pp. 2-29
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69
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0004235357
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Blatt, A. H., E.; Wiley: New York, Collect.
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Arndt, F. In Organic Syntheses; Blatt, A. H., E.; Wiley: New York, 1943; Collect. Vol. 2, pp 165–167, Note 3.
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(1943)
Organic Syntheses
, vol.2
, pp. 165-167
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Arndt, F.1
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