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Volumn 14, Issue 8, 2003, Pages 1037-1043

Diastereoselective synthesis of protected 4-epi-vancosamine from (S)-N-Boc-N,O-isopropylidene-α-methylserinal

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; AMINE; CHEMICAL COMPOUND; METHYL N,O DIBENZOYL 4 EPIVANCOSAMINE; N TERT BUTYLOXYCARBONYL N,O ISOPROPYLIDENE ALPHA METHYLSERINAL; UNCLASSIFIED DRUG;

EID: 0037453330     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00119-8     Document Type: Article
Times cited : (10)

References (41)
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    • Condensation of a dialdehyde, obtained from oxidation of methyl α-L-rhamnopyranoside, with basic nitroethane: (a) Brimacombe, J. S.; Doner, L. W. J. Chem. Soc., Perkin Trans. 1 1974, 62-65; (b) Brimacombe, J. S.; Mengech, A. S.; Saeed, M. S. Carbohydr. Res. 1979, 75, C5-C7; (c) Brimacombe, J. S.; Mengech, A. S. J. Chem. Soc., Perkin Trans. 1 1980, 2054-2060; (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr.Res. 1981, 93, 288-293.
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    • Condensation of a dialdehyde, obtained from oxidation of methyl α-L-rhamnopyranoside, with basic nitroethane: (a) Brimacombe, J. S.; Doner, L. W. J. Chem. Soc., Perkin Trans. 1 1974, 62-65; (b) Brimacombe, J. S.; Mengech, A. S.; Saeed, M. S. Carbohydr. Res. 1979, 75, C5-C7; (c) Brimacombe, J. S.; Mengech, A. S. J. Chem. Soc., Perkin Trans. 1 1980, 2054-2060; (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr.Res. 1981, 93, 288-293.
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    • Condensation of a dialdehyde, obtained from oxidation of methyl α-L-rhamnopyranoside, with basic nitroethane: (a) Brimacombe, J. S.; Doner, L. W. J. Chem. Soc., Perkin Trans. 1 1974, 62-65; (b) Brimacombe, J. S.; Mengech, A. S.; Saeed, M. S. Carbohydr. Res. 1979, 75, C5-C7; (c) Brimacombe, J. S.; Mengech, A. S. J. Chem. Soc., Perkin Trans. 1 1980, 2054-2060; (d) Ahmad, H. I.; Brimacombe, J. S.; Mengech, A. S.; Tucker, L. C. N. Carbohydr.Res. 1981, 93, 288-293.
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    • Synthesis of both enantiomers of 4-epi-vancosamine from L- and D-hexos-3-ulose intermediates: (a) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Funabashi, M. Chem. Lett. 1977, 1403-1406; (b) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Nagasawa, Y. Carbohydr. Res. 1979, 76, 67-78; (c) Yoshimura, J.; Matsuzawa, M.; Funabashi, M. Bull. Chem. Soc. Jpn. 1978, 51, 2064-2067; (d) Brimacombe, J. S.; Saeed, M. S.; Weakley, J. R. J. Chem. Soc., Perkin Trans. 1 1980, 2061-2064.
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    • Yoshimura, J.1    Matsuzawa, M.2    Sato, K.-I.3    Funabashi, M.4
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    • Synthesis of both enantiomers of 4-epi-vancosamine from L- and D-hexos-3-ulose intermediates: (a) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Funabashi, M. Chem. Lett. 1977, 1403-1406; (b) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Nagasawa, Y. Carbohydr. Res. 1979, 76, 67-78; (c) Yoshimura, J.; Matsuzawa, M.; Funabashi, M. Bull. Chem. Soc. Jpn. 1978, 51, 2064-2067; (d) Brimacombe, J. S.; Saeed, M. S.; Weakley, J. R. J. Chem. Soc., Perkin Trans. 1 1980, 2061-2064.
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    • Synthesis of both enantiomers of 4-epi-vancosamine from L- and D-hexos-3-ulose intermediates: (a) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Funabashi, M. Chem. Lett. 1977, 1403-1406; (b) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Nagasawa, Y. Carbohydr. Res. 1979, 76, 67-78; (c) Yoshimura, J.; Matsuzawa, M.; Funabashi, M. Bull. Chem. Soc. Jpn. 1978, 51, 2064-2067; (d) Brimacombe, J. S.; Saeed, M. S.; Weakley, J. R. J. Chem. Soc., Perkin Trans. 1 1980, 2061-2064.
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    • Synthesis of both enantiomers of 4-epi-vancosamine from L- and D-hexos-3-ulose intermediates: (a) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Funabashi, M. Chem. Lett. 1977, 1403-1406; (b) Yoshimura, J.; Matsuzawa, M.; Sato, K.-I.; Nagasawa, Y. Carbohydr. Res. 1979, 76, 67-78; (c) Yoshimura, J.; Matsuzawa, M.; Funabashi, M. Bull. Chem. Soc. Jpn. 1978, 51, 2064-2067; (d) Brimacombe, J. S.; Saeed, M. S.; Weakley, J. R. J. Chem. Soc., Perkin Trans. 1 1980, 2061-2064.
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    • Synthesis of the N-benzoyl derivatives of 4-epi-vancosamine from a chiral diol, prepared in fermenting baker's yeast from α-methylcinnamaldehyde and acetaldehyde: (a) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073-5076; (b) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225-248.
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    • Synthesis of the N-benzoyl derivatives of 4-epi-vancosamine from a chiral diol, prepared in fermenting baker's yeast from α-methylcinnamaldehyde and acetaldehyde: (a) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. Tetrahedron Lett. 1981, 22, 5073-5076; (b) Fronza, G.; Fuganti, C.; Grasselli, P.; Pedrocchi-Fantoni, G. J. Carbohydr. Chem. 1983, 2, 225-248.
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    • This duplication of signals in the NMR spectra has also been observed in other compounds that incorporate carbamate groups, see: (a) Ref. 13; (b) Parthasarthy, R.; Paul, B.; Korytnyk, W. J. Am. Chem. Soc. 1976, 98, 6634-6643; (c) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364; (d) Monache, G. D.; Di Giovanni, M. C.; Maggio, F.; Misiti, D.; Zappia, G. Synthesis 1995, 1155-1158.
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    • This duplication of signals in the NMR spectra has also been observed in other compounds that incorporate carbamate groups, see: (a) Ref. 13; (b) Parthasarthy, R.; Paul, B.; Korytnyk, W. J. Am. Chem. Soc. 1976, 98, 6634-6643; (c) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364; (d) Monache, G. D.; Di Giovanni, M. C.; Maggio, F.; Misiti, D.; Zappia, G. Synthesis 1995, 1155-1158.
    • (1987) J. Org. Chem. , vol.52 , pp. 2361-2364
    • Garner, P.1    Park, J.M.2
  • 32
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    • This duplication of signals in the NMR spectra has also been observed in other compounds that incorporate carbamate groups, see: (a) Ref. 13; (b) Parthasarthy, R.; Paul, B.; Korytnyk, W. J. Am. Chem. Soc. 1976, 98, 6634-6643; (c) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364; (d) Monache, G. D.; Di Giovanni, M. C.; Maggio, F.; Misiti, D.; Zappia, G. Synthesis 1995, 1155-1158.
    • (1995) Synthesis , pp. 1155-1158
    • Monache, G.D.1    Di Giovanni, M.C.2    Maggio, F.3    Misiti, D.4    Zappia, G.5
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    • Other attempts at oxidation, such as Swern conditions, failed.
    • Other attempts at oxidation, such as Swern conditions, failed.


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