A concise route to phytosphingosine from lyxose

Tetrahedron Letters

Volumn 44, Issue 28, 2003, Pages 5281-5283

  Lin, Chun Cheng ^a   Fan, Gang Ting ^a,b   Fang, Jim Min ^b  

^a INSTITUTE OF CHEMISTRY   (Taiwan)

^b NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; DEXTRO 2,3 O ISOPROPYLIDENE DEXTRO LYXOFURANOSE; LIPID; LYXOSE; PHYTOSPHINGOSINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; WITTIG REACTION;

EID: 0038345940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01281-4     Document Type: Article

References (43)

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20. For recent examples using amino acid precursors, see: (a) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (b) Takikawa, H.; Muto, S.-e.; Mori, K. Tetrahedron 1998, 54, 3141-3150; (c) Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670; (d) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113-2116; (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446; (f) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 1069-1078.
21. For recent examples using amino acid precursors, see: (a) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (b) Takikawa, H.; Muto, S.-e.; Mori, K. Tetrahedron 1998, 54, 3141-3150; (c) Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670; (d) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113-2116; (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446; (f) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 1069-1078.
22. For recent examples using amino acid precursors, see: (a) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (b) Takikawa, H.; Muto, S.-e.; Mori, K. Tetrahedron 1998, 54, 3141-3150; (c) Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670; (d) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113-2116; (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446; (f) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 1069-1078.
23. For recent examples using amino acid precursors, see: (a) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (b) Takikawa, H.; Muto, S.-e.; Mori, K. Tetrahedron 1998, 54, 3141-3150; (c) Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670; (d) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113-2116; (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446; (f) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 1069-1078.
24. For recent examples using amino acid precursors, see: (a) Azuma, H.; Tamagaki, S.; Ogino, K. J. Org. Chem. 2000, 65, 3538-3541; (b) Takikawa, H.; Muto, S.-e.; Mori, K. Tetrahedron 1998, 54, 3141-3150; (c) Imashiro, R.; Sakurai, O.; Yamashita, T.; Horikawa, H. Tetrahedron 1998, 54, 10657-10670; (d) Yoda, H.; Oguchi, T.; Takabe, K. Tetrahedron: Asymmetry 1996, 7, 2113-2116; (e) Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446; (f) Sugiyama, S.; Honda, M.; Komori, T. Liebigs Ann. Chem. 1990, 1069-1078.
25. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
26. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
27. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
28. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
29. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
30. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
31. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
32. For recent examples using sugar precursors, see: (a) Plettenburg, O.; Bodmer-Narkevitch, V.; Wong, C.-H. J. Org. Chem. 2002, 67, 4559-4564; (b) Luo, S.-Y.; Thopate, S. R.; Hsu, C.-Y.; Hung, S.-C. Tetrahedron Lett. 2002, 43, 4889-4892; (c) Graziani, A.; Passacantilli, P.; Piancatelli, G.; Tani, S. Tetrahedron: Asymmetry 2000, 11, 3921-3937; (d) Figueroa-Pérez, S.; Schmidt, R. R. Carbohydr. Res. 2000, 328, 95-102; (e) Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004; (f) Wee, A. G. H.; Tang, F. Tetrahedron Lett. 1996, 37, 6677-6680; (g) Li, Y.-L.; Mao, X.-H.; Wu, Y.-L. J. Chem. Soc., Perkin Trans. 1 1995, 1559-1563; (h) Matsumoto, K.; Ebata, T.; Matsushita, H. Carbohydr. Res. 1995, 279, 93-106.
33. For recent examples using various chiral precursors, see: (a) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Martin, C.; Prünck, W.; Bortolussi, M.; Bloch, R. Tetrahedron: Asymmetry 2000, 11, 1585-1592.
34. For recent examples using various chiral precursors, see: (a) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Martin, C.; Prünck, W.; Bortolussi, M.; Bloch, R. Tetrahedron: Asymmetry 2000, 11, 1585-1592.
35. For recent examples using various chiral precursors, see: (a) Nakamura, T.; Shiozaki, M. Tetrahedron 2001, 57, 9087-9092; (b) He, L.; Byun, H.-S.; Bittman, R. J. Org. Chem. 2000, 65, 7618-7626; (c) Martin, C.; Prünck, W.; Bortolussi, M.; Bloch, R. Tetrahedron: Asymmetry 2000, 11, 1585-1592.
36. D-Lyxose is not a usual and cheap sugar, but is also not a rare sugar.
37. Barbat J., Gelas J., Horton D. Carbohydr. Res. 219:1991;115-121.
38. 3) δ 0.88 (t, J=6.0 Hz, 3H), 1.26 (br, 24H), 1.35 (s, 3H), 1.35-1.50 (m, 1H overlapped with s at 1.45 ppm, 3H), 1.55-1.72 (m, 1H), 2.33 (d, J=6.0 Hz, 1H), 3.13-3.25 (m, 2H), 3.65-3.76 (m, 1H), 4.00-4.16 (m, 2H), 7.15-7.35 (m 9H), 7.35-7.50 (m, 6H).
39. Tuch A., Saniére M., Merrer Y.L., Depezay J.-C. Tetrahedron: Asymmetry. 7:1996;897-906.
40. 3) δ 0.91 (t, J=6.8 Hz, 3H), 1.29 (br, 30H overlapped with two s at 1.25 ppm, 3H, 1.28 ppm, 3H), 1.40-1.65 (m, 2H), 3.88 (dd, J=7.6, 10.0 Hz, 1H), 3.51 (ddd, J=2.4, 7.6, 9.2 Hz, 1H), 3.56 (dd, J=2.4, 9.6 Hz, 1H), 3.91 (dd, J=5.4, 8.8 Hz, 1H), 4.08-4.15 (m, 1H), 7.20-7.40 (m, 9H), 7.45-7.55 (m, 6H).
41. Kratzer B., Mayer T.G., Schmidt R.R. Eur. J. Org. Chem. 1998;291-298.
42. 18-phytosphingosine 1 was consisted with the given data of the following reference: Taguchi K., Murakami T. Tetrahedron. 55:1999;989-1004
43. Z).