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27
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51449099089
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note
-
By allylation (AllBr, NaH, DMF) of methyl 2,3-di-O-benzyl-l-arabinofuranoside, obtained according to Ref. 15.
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-
-
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28
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51449114932
-
-
note
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All new compounds gave correct elemental analyses and/or HRMS data.
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29
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13844314454
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Karanjule N.S., Markad S.D., Sharma T., Sabharwal S.G., Puranik V.G., and Dhavale D.D. J. Org. Chem. 70 (2005) 1356-1363
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Dhavale, D.D.6
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30
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-
0014040134
-
-
Experimental procedure for 5: To a solution of methyl 2,3-di-O-benzyl-β-l-arabino-pentodialdofuranoside:
-
Experimental procedure for 5: To a solution of methyl 2,3-di-O-benzyl-β-l-arabino-pentodialdofuranoside:. Tadahiro I., and Hiromichi S. Chem. Pharm. Bull. 15 (1967) 132-135
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Chem. Pharm. Bull.
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Tadahiro, I.1
Hiromichi, S.2
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31
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0014292832
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(170 mg, 0.50 mmol) in THF (3.4 mL) was added, at 0 °C, a 1 M solution of vinylmagnesium bromide in THF (2 mL). After stirring for 3 h at 0 °C and 12-14 h at rt, the reaction was quenched by adding saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with brine and dried over sodium sulfate. Solvents were evaporated, and purification on silica gel afforded compound 5 (130 mg, 71%) as a mixture of separable diastereoisomers (dr 28:72)
-
Hiromichi S., and Tadahiro I. Chem. Pharm. Bull. 16 (1968) 1129-1132 (170 mg, 0.50 mmol) in THF (3.4 mL) was added, at 0 °C, a 1 M solution of vinylmagnesium bromide in THF (2 mL). After stirring for 3 h at 0 °C and 12-14 h at rt, the reaction was quenched by adding saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The organic phase was separated, washed with brine and dried over sodium sulfate. Solvents were evaporated, and purification on silica gel afforded compound 5 (130 mg, 71%) as a mixture of separable diastereoisomers (dr 28:72)
-
(1968)
Chem. Pharm. Bull.
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Hiromichi, S.1
Tadahiro, I.2
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32
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17144426083
-
-
For a review on imino-C-disaccharides synthesis:
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For a review on imino-C-disaccharides synthesis:. Robina I., and Vogel P. Synthesis (2005) 675-702
-
(2005)
Synthesis
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Robina, I.1
Vogel, P.2
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33
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84889289469
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Imino-C-Disaccharides and Analogues: Synthesis and Biological Activity
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Compain P., and Martin O.R. (Eds), Wiley, Chichester
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Vogel P., Gerber-Lemaire S., and Juilleret-Jeannerat L. Imino-C-Disaccharides and Analogues: Synthesis and Biological Activity. In: Compain P., and Martin O.R. (Eds). Iminosugars: From Synthesis to Therapeutic Application (2007), Wiley, Chichester 87-123
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Iminosugars: From Synthesis to Therapeutic Application
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Vogel, P.1
Gerber-Lemaire, S.2
Juilleret-Jeannerat, L.3
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34
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0042766862
-
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For related imino-C-disaccharides precursors see:
-
For related imino-C-disaccharides precursors see:. Cardona F., Goti A., and Brandi A. Org. Lett. 5 (2003) 1475-1478
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Org. Lett.
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Cardona, F.1
Goti, A.2
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35
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41149177725
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Cardona F., Lalli C., Faggi C., Goti A., and Brandi A. J. Org. Chem. 73 (2008) 1999-2002
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Cardona, F.1
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Brandi, A.5
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36
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0036146424
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Marquis C., Cardona F., Robina I., Wurth G., and Vogel P. Heterocycles 56 (2002) 181-208
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Marquis, C.1
Cardona, F.2
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Wurth, G.4
Vogel, P.5
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33947185293
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Shing T.K.M., Wong W.F., Cheng H.M., Kwok W.S., and So K.H. Org. Lett. 9 (2007) 753-756
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Shing, T.K.M.1
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So, K.H.5
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41
-
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51449121736
-
-
note
-
Synthesis of compound 9: Methyl β-d-galactofuranoside (494 mg, 2.55 mmol) was dissolved in MeOH (30 mL). Dibutyltin oxide (1.27 g, 5.09 mmol) was then added and the reaction mixture was stirred for 4 h at 70 °C. After concentration under reduced pressure, the white foamy material was dissolved in THF (3.5 mL). After the addition of tetrabutylammonium iodide (940 mg, 2.54 mmol) and allyl bromide (488 μL, 5.61 mmol), the mixture was stirred overnight at rt and then for 48 h at 50 °C. After concentration under reduced pressure, purification on silica gel (EP/AcOEt 4/1 and then 2/1) afforded the desired compound 9 (382 mg, 64%) as a yellowish oil.
-
-
-
-
42
-
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51449106624
-
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Desvergnes, V.; Biltresse, S.; Martin, O.R. Conception et Synthèse d'Analogues du Galactofuranose. Presented at the National Organic Symposium of the French Chemical Society (JCO), Palaiseau, France, September 7-9, 2004; Abstract P268.
-
Desvergnes, V.; Biltresse, S.; Martin, O.R. Conception et Synthèse d'Analogues du Galactofuranose. Presented at the National Organic Symposium of the French Chemical Society (JCO), Palaiseau, France, September 7-9, 2004; Abstract P268.
-
-
-
-
44
-
-
51449087662
-
-
note
-
2O 7/4/0.1) afforded the desired cycloadduct.
-
-
-
-
48
-
-
0035166007
-
-
For tritylation of a related galactofuranoside, see:
-
For tritylation of a related galactofuranoside, see:. Pathak A.K., Pathak V., Seitz L., Maddry J.A., Gurcha S.S., Besra G.S., Suling W.J., and Reynolds R.C. Bioorg. Med. Chem. 9 (2001) 3129-3143
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Pathak, A.K.1
Pathak, V.2
Seitz, L.3
Maddry, J.A.4
Gurcha, S.S.5
Besra, G.S.6
Suling, W.J.7
Reynolds, R.C.8
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51
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20444497757
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See also: and reference cited therein
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See also:. Muzart J. Tetrahedron 61 (2005) 5955-6008 and reference cited therein
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Watson, A.A.1
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Lees, E.6
Asano, N.7
Kizu, H.8
Kato, A.9
Griffiths, R.C.10
Cairns, A.J.11
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