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Volumn 44, Issue 3, 2003, Pages 579-582

A new diorganozinc-based enantioselective access to truncated D-ribo-phytosphingosine

Author keywords

Diorganozinc reagent; Double asymmetric induction; Phytosphingosine

Indexed keywords

ALDEHYDE DERIVATIVE; ANTINEOPLASTIC AGENT; AZIDE; DEXTRO RIBOPHYTOSPHINGOSINE; EPOXIDE; ORGANIC COMPOUND; REAGENT; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

EID: 0037433961     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02526-1     Document Type: Article
Times cited : (10)

References (46)
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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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    • 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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    • 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.
    • (2000) Tetrahedron: Asymmetry , vol.11 , pp. 3921-3937
    • Graziani, A.1    Passacantilli, P.2    Piancatelli, P.3    Tani, S.4
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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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    • Santiago, F.-P.1    Schmidt, R.R.2
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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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    • 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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    • 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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    • 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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    • 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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    • 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.
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  • 33
    • 0012162364 scopus 로고    scopus 로고
    • 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.
  • 40
    • 0012162365 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 28b
    • 28b.
  • 42
    • 0012122706 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • 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 scopus 로고    scopus 로고
    • +
    • +.
  • 46
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    • 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.
    • (2000) Methods Enzymol. , vol.312 , pp. 407-420
    • Luberto, C.1    Hannun, Y.A.2


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