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Volumn 4, Issue 3, 2007, Pages 201-216

Synthesis of carbasugars based on ring closing metathesis: 2000-2006

Author keywords

Carbaarabinofuranoses; Cross metathesis; Cyclophellitol; Trehazolamine; Valienamine

Indexed keywords

CARBOHYDRATES; MOLECULES;

EID: 34548136568     PISSN: 1570193X     EISSN: None     Source Type: Journal    
DOI: 10.2174/157019307781369931     Document Type: Article
Times cited : (43)

References (197)
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    • For the synthesis of heterocyclic compounds using RCM see: f, Gribble, G.N, Joule, J.A. Eds, Pergamon, Oxford
    • For the synthesis of heterocyclic compounds using RCM see: (f) que Walters, M.A. in Progress in Heterocyclic Chemistry, Gribble, G.N.; Joule, J.A. Eds.; Pergamon, Oxford, 2003.
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    • For further references on the synthesis of functionalized cyclopentene derivatives, intermediates for the preparation of carbanucleosides, using RCM reactions, see: b
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    • For a discussion of the theoretical basis for the design of these catalysts: see Ref 22b (in particular pp. 3019-3020) and references therein.
    • For a discussion of the theoretical basis for the design of these catalysts: see Ref 22b (in particular pp. 3019-3020) and references therein.
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    • Oligosaccharide analogs containing carbasugar residues have been shown to be glycosyl transferase substrates, see: (a) Ogawa, S, Furuya, T, Tsunoda, H, Hindsgaul, O, Stangier, K, Palcic, M.M. Carbohydr. Res, 1995, 271, 197
    • Oligosaccharide analogs containing carbasugar residues have been shown to be glycosyl transferase substrates, see: (a) Ogawa, S.; Furuya, T.; Tsunoda, H.; Hindsgaul, O.; Stangier, K.; Palcic, M.M. Carbohydr. Res., 1995, 271, 197.
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    • For the synthesis of di- and trisaccharides containing modified arabinofuranosyl moieties, see: d
    • For the synthesis of di- and trisaccharides containing modified arabinofuranosyl moieties, see: (d) Cociorva, O.M.; Gurcha, S.S.; Besra, G.S.; Lowary, T.L. Bioorg. Med. Chem., 2005, 13, 1369.
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    • It should be pointed out that in this paper an olefin CM reaction was applied to the synthesis of a C-disaccharide analog of α-D-Araf-(1-5)-a-D-Araf moiety. For the synthesis of C-phosphonate analogs of decaprenolphosphoarabinose, an intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinogalactan and lipoarabinomannan, see: (g) Centrone, C.A, Lowary, T.L. J. Org. Chem, 2002, 67, 8862
    • It should be pointed out that in this paper an olefin CM reaction was applied to the synthesis of a C-disaccharide analog of α-D-Araf-(1-5)-a-D-Araf moiety. For the synthesis of C-phosphonate analogs of decaprenolphosphoarabinose, an intermediate in the biosynthesis of mycobacterial arabinogalactan and lipoarabinogalactan and lipoarabinomannan, see: (g) Centrone, C.A.; Lowary, T.L. J. Org. Chem., 2002, 67, 8862.
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    • This is particularly important considering the resurgence of tuberculosis and the emergence of drug resistance of Mycobacterium tuberculosis. See, for instance, Wade, M.M, Zhang, Y. Front. Biosci, 2004, 9, 975
    • This is particularly important considering the resurgence of tuberculosis and the emergence of drug resistance of Mycobacterium tuberculosis. See, for instance, Wade, M.M.; Zhang, Y. Front. Biosci., 2004, 9, 975.
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    • The selection of this catalyst was based on previous work by the same authors regarding the RCM reaction of functionalized diene systems. See, a Seepersaud, M, Bucala, R; Al-Abed, Y. Z. Naturforsh. 1999, 54b, 565
    • The selection of this catalyst was based on previous work by the same authors regarding the RCM reaction of functionalized diene systems. See, (a) Seepersaud, M.; Bucala, R; Al-Abed, Y. Z. Naturforsh. 1999, 54b, 565.
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    • Callam and Lowary (Ref 41), improved the transformation (12)→(13) and rendered the final product available in a multigram scale.
    • (c) Callam and Lowary (Ref 41), improved the transformation (12)→(13) and rendered the final product available in a multigram scale.
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    • The synthesis of 1,2-O-isopropylidene-4a-carba-β-L-xylofuranose has also been carried out from a cyclopentene derivative obtained in turn via RCM of a carbohydrate-derived 1,6-diene. See: Ovaa, H.; Lastdrager, B.; Codeé, J.D.C.; van der Marel, G.A.; Overkleeft; H.S.; van Boom, J.H. J. Chem. Soc. Berkin Trans. 1, 2002, 2370.
    • (b) The synthesis of 1,2-O-isopropylidene-4a-carba-β-L-xylofuranose has also been carried out from a cyclopentene derivative obtained in turn via RCM of a carbohydrate-derived 1,6-diene. See: Ovaa, H.; Lastdrager, B.; Codeé, J.D.C.; van der Marel, G.A.; Overkleeft; H.S.; van Boom, J.H. J. Chem. Soc. Berkin Trans. 1, 2002, 2370.
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    • For a discussion on the influence of the nature of the O-protecting group in the allylic position on the stereoselectivity of epoxidation reactions, see: (a) Aceña, J.L, Arjona, O, Fernández de la Pradilla, R, Plumet, J, Viso, A. J. Org. Chem, 1994, 59, 6419
    • For a discussion on the influence of the nature of the O-protecting group in the allylic position on the stereoselectivity of epoxidation reactions, see: (a) Aceña, J.L.; Arjona, O.; Fernández de la Pradilla, R.; Plumet, J.; Viso, A. J. Org. Chem., 1994, 59, 6419.
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    • This is according to the authors, the first example of an asymmetric crotonyl aldol reaction through the use of chlorotitanium enolate
    • This is according to the authors, "the first example of an asymmetric crotonyl aldol reaction through the use of chlorotitanium enolate"
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    • Chelation effects play an important role in the course of metathetical reactions both from the chemo- and stereoselective points of view. For a discussion see see ref. 25, pp 1906-1907, and references therein
    • Chelation effects play an important role in the course of metathetical reactions both from the chemo- and stereoselective points of view. For a discussion see see ref. 25, pp 1906-1907, and references therein.
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    • The irreversible inhibition of β-glucosidases by cyclophellitol appears to be a consequence of the protonation and subsequent ring-opening of the oxirane moiety by a carboxylate in the active site of the enzyme. See ref. 9 and: Withers, S.G, Umezawa, K. Biochem. Biopyhs. Res. Commun, 1991, 177, 532
    • The irreversible inhibition of β-glucosidases by cyclophellitol appears to be a consequence of the protonation and subsequent ring-opening of the oxirane moiety by a carboxylate in the active site of the enzyme. See ref. 9 and: Withers, S.G.; Umezawa, K. Biochem. Biopyhs. Res. Commun., 1991, 177, 532.
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    • The total diastereoselectivity of the reaction might be explained by invoking an In-chelated intermediate
    • The total diastereoselectivity of the reaction might be explained by invoking an In-chelated intermediate.
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    • Valienamine is a component of several oligosaccharides exhibiting strong enzyme inhibitory activities. For reviews, see: (a) Chen, X, Fan, Y, Zheng, Y, Shen, Y. Chem. Rev, 2003, 103, 1955
    • Valienamine is a component of several oligosaccharides exhibiting strong enzyme inhibitory activities. For reviews, see: (a) Chen, X.; Fan, Y.; Zheng, Y.; Shen, Y. Chem. Rev., 2003, 103, 1955.
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    • See, for instance: (a) Fukase, H.; Horii, S. J. Org. Chem., 1992, 57, 3651.
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    • The stereochemical result of this reaction should be compared with that obtained from carbafuranose (8) see Scheme 2
    • The stereochemical result of this reaction should be compared with that obtained from carbafuranose (8) see Scheme 2.
  • 145
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    • Attempts at differentiatingthe two hydroxyl groups of (107) using benzoyl chloride or p-methoxybenzyl chloride were not successful.
    • Attempts at differentiatingthe two hydroxyl groups of (107) using benzoyl chloride or p-methoxybenzyl chloride were not successful.
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    • In addition to their role as chiral auxiliary, the hydrophobic nature of the sultam moiety allows for the recovery of the resulting triols from water by extraction with organic solvents
    • In addition to their role as chiral auxiliary, the hydrophobic nature of the sultam moiety allows for the recovery of the resulting triols from water by extraction with organic solvents.
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    • For a previous synthesis of this compound, see: Horneman, A.M.; Lundt, I. J. Org. Chem., 1998, 63, 1919.
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    • Selected synthesis: (a) Ogawa, S.; Toyokuni, T.; Omata, M.; Chida, N.; Suami, T. Bull. Chem. Soc. Jpn., 1980, 53, 455 (racemic).
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    • From sugars to carba-sugars
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    • Gómez, A.M.; Company, M.D., Uriel, C.; Valverde, S.; López, J.C. Tetrahedron Lett., 2007, 48, 1645.
    • (j) Gómez, A.M.; Company, M.D., Uriel, C.; Valverde, S.; López, J.C. Tetrahedron Lett., 2007, 48, 1645.
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    • For recent contributions on the synthesis of carbasugar analogs and carbanucleosides by RCM, that lay beyond the scope of this review, see: a
    • For recent contributions on the synthesis of carbasugar analogs and carbanucleosides by RCM, that lay beyond the scope of this review, see: (a) Roy, B.G.; Maity, J.K.; Drew, M.G.B.; Achari, B.; Mandal, S.B. Tetrahedron Lett., 2006, 47, 8821.
    • (2006) Tetrahedron Lett , vol.47 , pp. 8821
    • Roy, B.G.1    Maity, J.K.2    Drew, M.G.B.3    Achari, B.4    Mandal, S.B.5
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    • A review has recently appeared: Arjona, O.; Gómez, A.M.; López, J.C.; Plumet, J. Chem. Rev., 2007, 107, 1919.
    • A review has recently appeared: Arjona, O.; Gómez, A.M.; López, J.C.; Plumet, J. Chem. Rev., 2007, 107, 1919.


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