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2
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34548172190
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Angew. Chem. 2001, 113, 1624.
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Angew1
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3
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0036462603
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(b) Gruner, S. A. W.; Locardi, E.; Lohof, E.; Kessler, H. Chem. Rev. 2002, 102, 491.
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, pp. 491
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Gruner, S.A.W.1
Locardi, E.2
Lohof, E.3
Kessler, H.4
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5
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34548173439
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Angew. Chem. 2002, 114, 240.
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Chem
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, pp. 240
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Angew1
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7
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16244405908
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(b) Helms, M.; Schade, W.; Pulz, R.; Watanabe, T.; Al-Harrasi, A.; Fisera, L.; Hlobilová, I.; Zahn, G.; Reissig, H.-U. Eur. J. Org. Chem. 2005, 1003.
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Eur. J. Org. Chem
, pp. 1003
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Helms, M.1
Schade, W.2
Pulz, R.3
Watanabe, T.4
Al-Harrasi, A.5
Fisera, L.6
Hlobilová, I.7
Zahn, G.8
Reissig, H.-U.9
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9
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33846509764
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Angew. Chem. 2005, 117, 6383.
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(2005)
Chem
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, pp. 6383
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Angew1
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10
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34548172683
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Dissertation; Freie Universität: Berlin
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Al-Harrasi, A. Dissertation; Freie Universität: Berlin, 2005.
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(2005)
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Al-Harrasi, A.1
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11
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34548186404
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Compound 4b is obtained by the reduction of the corresponding TBS-protected ketone (see ref. 3) followed by protection of the secondary alcohol with BnBr.
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Compound 4b is obtained by the reduction of the corresponding TBS-protected ketone (see ref. 3) followed by protection of the secondary alcohol with BnBr.
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12
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34548175191
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Typical Procedure for the Conversion of 5 into 6 Alcohol 5 (0.320 g, 0.629 mmol) was dissolved in anhyd DMF (10 mL, then PDC (0.946 g, 2.52 mmol) and Ac2O (0.24 mL, 2.5 mmol) were added. The mixture was stirred for 12 h at r.t. Then, Et2O and H2O were added and the layers were separated. The organic layer was successively washed with H2O, dried (MgSO4, and the solvent was removed under reduced pressure. Purification by column chromatography (silica gel, hexane-EtOAc, 4:1 to 1:1) yielded 0.250 g (79, of 6 as a colorless solid. Analytical Data for tert-Butyl (1S,4S,5R,8S)-8-Benzyloxy-4-(tert-buryl-dimethylsiloxymethyl)-2,2-dimethyl-7-oxo-3-oxa-6- azabicyclo[3.2.1]octane-6-carboxylate (6, α]D22 +14.1 (c 1.43, CHCl3, mp 64-65°C. 1H NMR 500 MHz, CDC
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6Si (505.3): C, 64.12; H, 8.57; N, 2.77. Found: C, 64.22; H, 8.75; N, 2.78.
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-
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13
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0000420816
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(a) Campagne, J.-M.; Coste, J.; Jouin, P. J. Org. Chem. 1995, 60, 5214.
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(1995)
J. Org. Chem
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, pp. 5214
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Campagne, J.-M.1
Coste, J.2
Jouin, P.3
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14
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49549139072
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(b) Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
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(1975)
Tetrahedron Lett
, pp. 1219
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Castro, B.1
Dormoy, J.R.2
Evin, G.3
Selve, C.4
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15
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33748324475
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Veljkovic, I.; Zimmer, R.; Reissig, H.-U.; Brüdgam, I.; Hartl, H. Synthesis 2006, 2677.
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(2006)
Synthesis
, pp. 2677
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-
Veljkovic, I.1
Zimmer, R.2
Reissig, H.-U.3
Brüdgam, I.4
Hartl, H.5
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17
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34548146542
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Angew. Chem. 1963, 75, 604.
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(1963)
Chem
, vol.75
, pp. 604
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Angew1
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18
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0037099395
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(b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem. Int. Ed. 2002, 41, 2596;
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(2002)
Angew. Chem. Int. Ed
, vol.41
, pp. 2596
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Rostovtsev, V.V.1
Green, L.G.2
Fokin, V.V.3
Sharpless, K.B.4
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19
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0013064237
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Angew. Chem. 2002, 114, 2708.
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(2002)
Chem
, vol.114
, pp. 2708
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Angew1
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20
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0037012920
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(c) Tornoe, C. W.; Christensen, C.; Meldal, M. J. Org. Chem. 2002, 67, 3057.
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(2002)
J. Org. Chem
, vol.67
, pp. 3057
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Tornoe, C.W.1
Christensen, C.2
Meldal, M.3
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22
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34548178500
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3 is not explosive and is stable at r.t.
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3 is not explosive and is stable at r.t.
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23
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0030593609
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Alper, P. B.; Hung, S.-C.; Wong, C.-H. Tetrahedron Lett. 1996, 37, 6029.
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(1996)
Tetrahedron Lett
, vol.37
, pp. 6029
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Alper, P.B.1
Hung, S.-C.2
Wong, C.-H.3
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24
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34548145106
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Typical Procedure for the Conversion of 7 into 10 To a solution of amino alcohol 7 (150 mg, 0.73 mmol) in MeOH-H2O (2:1, 3 mL) at r.t. were added CuSO4·5H2O (18 mg, 0.073 mmol, 1 M solution in H2O) and K2CO3 (101 mg, 0.73 mmol, followed by slow addition of Nf-N3 (475 mg, 1.46 mmol) via syringe. The mixture was stirred for 24 h, then glycine hydrochloride (554 mg, 5 mmol) was added in order to quench the reaction mixture and the suspension was stirred for another 24 h. The mixture was filtered and the solvents were removed. The crude solid was dissolved in pyridine (6 mL) and cooled to 0°C. Then DMAP (3 mg, 0.02 mmol) and Ac2O (0.69 mL, 7.3 mmol) were added and the mixture was stirred at r.t. for 12 h. The residue was taken up in Et2O and washed with a 1 M solution of HCl and brine followed by a sat. solution of NaHCO3. The organic layer was dried MgSO
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+: 314.1349; found: 314.1352.
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25
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4444324951
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Chan, T. R.; Hilgraf, R.; Sharpless, K. B.; Fokin, V. V. Org. Lett. 2004, 6, 2853.
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(2004)
Org. Lett
, vol.6
, pp. 2853
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Chan, T.R.1
Hilgraf, R.2
Sharpless, K.B.3
Fokin, V.V.4
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26
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33749507838
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Groothuys, S.; Kuijpers, B. H. M.; Quaedflieg, P. J. L. M.; Roelen, H. C. P. F.; Wiertz, R. W.; Blaauw, R. H.; van Delft, F. L.; Rutjes, F. P. J. T. Synthesis 2006, 3146.
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(2006)
Synthesis
, pp. 3146
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Groothuys, S.1
Kuijpers, B.H.M.2
Quaedflieg, P.J.L.M.3
Roelen, H.C.P.F.4
Wiertz, R.W.5
Blaauw, R.H.6
van Delft, F.L.7
Rutjes, F.P.J.T.8
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27
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34548148681
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Typical Procedure for the Conversion of 10 into 14 To a solution of azide 10 (15 mg, 42 μmol) and phenyl acetylene 12 (5.0 μL, 42 μmol) in MeCN (0.78 mL) were added solutions of Et3N (840 μL, 8.4 μmol, 10 mM solution in MeCN, TBTA (8.4 μmol, 840 μL of a 10 mM solution in MeCN, and CuI (8.4 μmol, 840 μL of a 10 mM solution in MeCN, Argon was bubbled through the mixture for 15 min and the reaction was stirred for 24 h at 40°C. Then H2O (5 mL) and EtOAc (5 mL) were added. The organic layer was separated and the aqueous layer was extracted with EtOAc (2 x 3 mL, The combined organic layers were dried over MgSO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, hexane-EtOAc, 6:4 to pure EtOAc) to give 14 (18 mg, 90% yield) as a colorless solid. Analytical Data for 3S,4S,5R,6S, Acetic A
-
+: 460.2078; found: 460.2091.
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28
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27744431508
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Peri, F.; Marinzi, C.; Barath, M.; Granucci, F.; Urbano, M.; Nicotra, F. Bioorg. Med. Chem. 2006, 14, 190.
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(2006)
Bioorg. Med. Chem
, vol.14
, pp. 190
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Peri, F.1
Marinzi, C.2
Barath, M.3
Granucci, F.4
Urbano, M.5
Nicotra, F.6
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30
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31144455167
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For examples of triazole-linked pseudo-oligosaccharides, see: (a) Hotha, S, Kashyap, S. J. Org. Chem. 2006, 71, 364
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For examples of triazole-linked pseudo-oligosaccharides, see: (a) Hotha, S.; Kashyap, S. J. Org. Chem. 2006, 71, 364.
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32
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34548152289
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These compounds are currently being tested as selectin binding substrates in collaboration with J. Dernedde, R. Tauber, Charité- Universitätsmedizin Berlin, CBF, Zentralinstitut für Laboratoriumsmedizin und Pathobiochemie
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These compounds are currently being tested as selectin binding substrates in collaboration with J. Dernedde, R. Tauber, Charité- Universitätsmedizin Berlin, CBF, Zentralinstitut für Laboratoriumsmedizin und Pathobiochemie.
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