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Recent reviews of metabolism and biological functions of sphingolipids: (a) Hannun, Y. A.; Luberto, C.; Argraves, K. M. Biochemistry 2001, 40, 4893-903; (b) Huwiler, A.; Kolter, T.; Pfeilschifter, J.; Sandhoff, K. Biochim. Biophys. Acta 2000, 1485, 63-99.
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Recent reviews of metabolism and biological functions of sphingolipids: (a) Hannun, Y. A.; Luberto, C.; Argraves, K. M. Biochemistry 2001, 40, 4893-903; (b) Huwiler, A.; Kolter, T.; Pfeilschifter, J.; Sandhoff, K. Biochim. Biophys. Acta 2000, 1485, 63-99.
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0023949069
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For their abundance in skin, see: (a) Wertz, P. W.; Swartzendruber, D. C.; Madison, K. C.; Downing, D. T. J. Invest. Dermatol. 1987, 89, 419-425. For their role in the epidermal water permeability barrier, see: (b) Landmann, L. Anat. Embryol. 1988, 178, 1-13.
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14
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12944255911
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Gonzales-Aseguinolaza G., de Oliveira C., Tomaska M., Hong S., Bruna-Romero O., Nakayama T., Taniguchi M., Bendelac A., Van Kaer L., Koezuka Y., Tsuji M. Proc. Natl. Acad. Sci. USA. 97:2000;8461-8466.
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Nakayama, T.6
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Tsuji, M.11
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0036644101
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Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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Tetrahedron Lett.
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Luo, S.-Y.1
Thopate, S.R.2
Hsu, C.-Y.3
Hung, S.-C.4
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16
-
-
0034602357
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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J. Org. Chem.
, vol.65
, pp. 7618-7626
-
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He, L.1
Byun, H.-S.2
Bittman, R.3
-
17
-
-
0034596034
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2000)
J. Org. Chem.
, vol.65
, pp. 3538-3541
-
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Azuma, H.1
Tamagaki, S.2
Ogino, K.3
-
18
-
-
0034612945
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2000)
Tetrahedron: Asymmetry
, vol.11
, pp. 3921-3937
-
-
Graziani, A.1
Passacantilli, P.2
Piancatelli, P.3
Tani, S.4
-
19
-
-
0038399264
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2000)
Carbohydr. Res.
, vol.328
, pp. 95-102
-
-
Santiago, F.-P.1
Schmidt, R.R.2
-
20
-
-
0037118355
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2002)
Org. Lett.
, vol.4
, pp. 1719-1722
-
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Ndakala, A.J.1
Hashemzadeh, M.2
So, R.C.3
Howell, A.R.4
-
21
-
-
0035968851
-
-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2001)
Tetrahedron
, vol.57
, pp. 9087-9092
-
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Nakamura, T.1
Shiozaki, M.2
-
22
-
-
0034707381
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-
Recent references concerning synthesis of natural D-ribo-phytosphingosine: (a) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (c) Graziani, A.; Passacantilli, P.; Piancatelli, P.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Santiago, F.-P.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102. Recent references concerning unnatural diastereomers: (d) Ndakala, A. J.; Hashemzadeh, M.; So, R. C.; Howell, A. R. Org. Lett. 2002, 4, 1719-1722; (e) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (f) Fernandes, R. A.; Kumar, P. Tetrahedron Lett. 2000, 41, 10309-10312.
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(2000)
Tetrahedron Lett.
, vol.41
, pp. 10309-10312
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Fernandes, R.A.1
Kumar, P.2
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23
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0034602274
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Recent references concerning structural variations in the sphingosine and sphinganine series: (a) Chun, J.; He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7634-7640; (b) Van Overmeire, I.; Boldin, S. A.; Venkataraman, K.; Zisling, R.; De Jonghe, S.; Van Calenbergh, S.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 2000, 43, 4189-4199.
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J. Org. Chem.
, vol.65
, pp. 7634-7640
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Chun, J.1
He, L.2
Byun, H.-S.3
Bittman, R.4
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24
-
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0034597611
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Recent references concerning structural variations in the sphingosine and sphinganine series: (a) Chun, J.; He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7634-7640; (b) Van Overmeire, I.; Boldin, S. A.; Venkataraman, K.; Zisling, R.; De Jonghe, S.; Van Calenbergh, S.; De Keukeleire, D.; Futerman, A. H.; Herdewijn, P. J. Med. Chem. 2000, 43, 4189-4199.
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J. Med. Chem.
, vol.43
, pp. 4189-4199
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Van Overmeire, I.1
Boldin, S.A.2
Venkataraman, K.3
Zisling, R.4
De Jonghe, S.5
Van Calenbergh, S.6
De Keukeleire, D.7
Futerman, A.H.8
Herdewijn, P.9
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29
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0036090874
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The addition of alkymagnesium reagents to α,β-epoxyaldehyde is known to be poorly anti-selective except in the presence of a chelating agent, as recently shown:
-
The addition of alkymagnesium reagents to α,β-epoxyaldehyde is known to be poorly anti-selective except in the presence of a chelating agent, as recently shown: Righi G., Ronconi S., Bonini C. Eur. J. Org. Chem. 2002;1573-1577.
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Eur. J. Org. Chem.
, pp. 1573-1577
-
-
Righi, G.1
Ronconi, S.2
Bonini, C.3
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31
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0032570482
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-
For the use of dihexylzinc in the preparation of a truncated dihydrosphingosine, see:
-
For the use of dihexylzinc in the preparation of a truncated dihydrosphingosine, see: Villard R., Fotiadu F., Buono G. Tetrahedron: Asymmetry. 1998;607-611.
-
(1998)
Tetrahedron: Asymmetry
, pp. 607-611
-
-
Villard, R.1
Fotiadu, F.2
Buono, G.3
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33
-
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0012162364
-
-
Monosilylation of butyne-1,4-diol was achieved with 80% yield based on the chlorosilane (5 equiv. butyne-1,4-diol, 1 equiv. NaH, THF, rt, 20 h) but the subsequent LAH or Red-Al triple bond reduction never exceeded 50% yield.
-
Monosilylation of butyne-1,4-diol was achieved with 80% yield based on the chlorosilane (5 equiv. butyne-1,4-diol, 1 equiv. NaH, THF, rt, 20 h) but the subsequent LAH or Red-Al triple bond reduction never exceeded 50% yield.
-
-
-
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37
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0026650218
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Takahashi H., Kawakita T., Ohno M., Yoshioka M., Kobayashi S. Tetrahedron. 48:1992;5691-5700.
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(1992)
Tetrahedron
, vol.48
, pp. 5691-5700
-
-
Takahashi, H.1
Kawakita, T.2
Ohno, M.3
Yoshioka, M.4
Kobayashi, S.5
-
40
-
-
0012162365
-
-
Based on HPLC analysis of the mixture of regioisomers (Merck Licrospher 12 μm, petroleum ether/isopropanol, 95/5). The two compounds were separated by MPLC column chromatography (silica gel 15-40 μm, petroleum ether/isopropanol, 97.5/2.5).
-
Based on HPLC analysis of the mixture of regioisomers (Merck Licrospher 12 μm, petroleum ether/isopropanol, 95/5). The two compounds were separated by MPLC column chromatography (silica gel 15-40 μm, petroleum ether/isopropanol, 97.5/2.5).
-
-
-
-
41
-
-
0012161536
-
-
28b
-
28b.
-
-
-
-
42
-
-
0012122706
-
-
The acetonide derived from the minor regioisomer displays a quaternary ketalic carbon at 100.9 ppm.
-
The acetonide derived from the minor regioisomer displays a quaternary ketalic carbon at 100.9 ppm.
-
-
-
-
44
-
-
0012121958
-
-
Based on HPLC analysis of the mixture of regioisomers (Waters Novapack Si, petroleum ether/dichloromethane/ethyl acetate, 85/9/6). This mixture was used without separation.
-
Based on HPLC analysis of the mixture of regioisomers (Waters Novapack Si, petroleum ether/dichloromethane/ethyl acetate, 85/9/6). This mixture was used without separation.
-
-
-
-
45
-
-
0012125959
-
-
+
-
+.
-
-
-
-
46
-
-
0033793071
-
-
Review of these important water soluble analogs:
-
Review of these important water soluble analogs: Luberto C., Hannun Y.A. Methods Enzymol. 312:2000;407-420.
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(2000)
Methods Enzymol.
, vol.312
, pp. 407-420
-
-
Luberto, C.1
Hannun, Y.A.2
|