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Volumn 70, Issue 1, 2005, Pages 24-38

Septanose carbohydrates: Synthesis and conformational studies of methyl α-D-glycero-D-idoseptanoside and methyl β-D-glycero-D-guloseptanoside

Author keywords

[No Author keywords available]

Indexed keywords

CHARACTERIZATION; GLUCOSE; ISOMERS; MONTE CARLO METHODS; NUCLEAR MAGNETIC RESONANCE; SOLUTIONS; SOLVENTS; SYNTHESIS (CHEMICAL);

EID: 12144277460     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048932z     Document Type: Article
Times cited : (57)

References (111)
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    • Thiophenyl glycosides: (a) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281. (b) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361. Thioethyl glycosides: (c) Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064. Glycosyl phosphates: (d) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211.
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    • Thiophenyl glycosides: (a) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281. (b) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361. Thioethyl glycosides: (c) Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064. Glycosyl phosphates: (d) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211.
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    • Thiophenyl glycosides: (a) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281. (b) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361. Thioethyl glycosides: (c) Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064. Glycosyl phosphates: (d) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 10064
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    • 0033614879 scopus 로고    scopus 로고
    • Thiophenyl glycosides: (a) Boulineau, F. P.; Wei, A. Org. Lett. 2002, 4, 2281. (b) Gordon, D. M.; Danishefsky, S. J. Carbohydr. Res. 1990, 206, 361. Thioethyl glycosides: (c) Seeberger, P. H.; Eckhardt, M.; Gutteridge, C. E.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10064. Glycosyl phosphates: (d) Plante, O. J.; Andrade, R. B.; Seeberger, P. H. Org. Lett. 1999, 1, 211.
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    • note
    • 3OH directly after its preparation. See the Supporting Information for the NMR spectra of 5.
  • 42
  • 65
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    • For discussion of the anomeric effect in seven-membered rings see ref 16a and: (a) Désuets, S.; St-Jacques, M. J. Am. Chem. Soc. 1987, 109, 1641. (b) Désuets, S.; St-Jacques, M. Can. J. Chem. 1992, 70, 2650.
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    • For discussion of the anomeric effect in seven-membered rings see ref 16a and: (a) Désuets, S.; St-Jacques, M. J. Am. Chem. Soc. 1987, 109, 1641. (b) Désuets, S.; St-Jacques, M. Can. J. Chem. 1992, 70, 2650.
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    • The classification of these O-H⋯ interactions as hydrogen bonds is based on the calculated bond distances and angles. Topologically, hydrogen bonds can be characterized based on minima in the overall electron density as demonstrated by: Klein, R. A. J. Am. Chem. Soc. 2002, 124, 13931.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 13931
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    • note
    • The method for determining the coefficients in eqs 1-3 is described in the Experimental Section.


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