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Novel Methyl 4,6-O-benzylidene-3-ketoglucopyranosid-fused γ-lactam: Synthesis and Crystal Structure

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Abstract

The title compound methyl 4,6-O-benzylidene-3-ketoglucopyranosid-fused γ-lactam was synthesized from 2-oxoglucopyranoside in one pot via multi-step reaction sequence under mild conditions. It was characterized by HRMS, 1H and 13C-NMR, IR, elemental analysis and single crystal X-ray diffraction. The crystal belongs to orthorhombic P2(1)2(1)2(1) space group with unit cell parameters a = 6.1840 (12) Å, b = 10.372 (2) Å, c = 25.702 (5) Å, V = 1648.5 (6) Å3, Z = 4, Dc = 1.343 Mg/m3, λ = 0.71073 Å, μ(Mo Kα) = 0.102 mm−1, F(000) = 704. X-ray diffraction analysis reveals that the compound adopts chair-chair conformation. The newly formed γ-lactam moiety is fused to glucopyranoside ring by C2 to form spirosugar. The crystal structure is stabilized by N–H···O2 hydrogen bond.

Graphical Abstract

Novel methyl 4,6-O-benzylidene-3-ketoglucopyranosid-fused γ-lactam was synthesized and characterized by HRMS, 1H and 13C-NMR, IR, elemental analysis and single crystal X-ray diffraction.

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References

  1. Hill MW, Reddy PA, Covey DF, Rothman SMJ (1998) J Neurosci 18:5103

    CAS  Google Scholar 

  2. Hill MW, de la Cruz MAM, Covey DF, Rothman SM (1999) Epilepsy Res 37:121

    Article  CAS  Google Scholar 

  3. Williams KL, Tucker JB, White G, Weiss DS, Ferrendelli JA, Covey DF, Krause JE, Rothman SM (1997) Mol Pharmacol 52:114

    CAS  Google Scholar 

  4. Maksay G, Molnár P, Gruber L (1994) Eur J Pharmacol 288:61

    Article  CAS  Google Scholar 

  5. Hill MW, Reddy PA, Covey DF, Rothman SM (1998) J Pharmacol Exp Ther 285:1303

    CAS  Google Scholar 

  6. Rekatas GV, Tani EK, Demopoulos VJ, Kourounakis PN (2000) Drug Dev Res 51:143

    Article  CAS  Google Scholar 

  7. Sasaki H, Mori Y, Nakamura J, Shibasaki J (1991) J Med Chem 34:628

    Article  CAS  Google Scholar 

  8. Jehle T, Feuerstein TJ, Lagreze WA (2001) Ophthalmologe 98:237

    Article  CAS  Google Scholar 

  9. Wall GM, Baker JK (1989) J Med Chem 32:1340

    Article  CAS  Google Scholar 

  10. Schweizer F, Otter A, Hindsgaul O (2001) Synlett 11:1743

    Article  Google Scholar 

  11. Schweizer F, Hindsgaul O (2006) Carbohydr Res 341:1730

    Article  CAS  Google Scholar 

  12. Hanessian S (1969) J Org Chem 34:675

    Article  CAS  Google Scholar 

  13. Zbignlew K, Wang F, Czestaw B, Marek C (1989) Tetrahedron Lett 30:5171

    Article  Google Scholar 

  14. Moreaux V, Warren H, Williams JM (1997) Tetrahedron Lett 38:4655

    Article  CAS  Google Scholar 

  15. Izquierdo I, Plaza MT, Robles R, Mota AJ (2000) Tetrahedron Asymm 11:4509

    Article  CAS  Google Scholar 

  16. Loukou C, Tosin M, Müller-Bunz H, Murphy PV (2007) Carbohydr Res 342:1953

    Article  CAS  Google Scholar 

  17. Araujo AC, Nicotra F, Costa B, Giagnoni G, Cipolla L (2008) Carbohydr Res 343:1840

    Article  CAS  Google Scholar 

  18. Liu HM, Tsuda Y (1996) Chem Pharm Bull 44:80

    CAS  Google Scholar 

  19. Liu HM, Xu W, Liu ZZ (2001) Carbohydr Res 331:229

    Article  CAS  Google Scholar 

  20. Liu HM, Zhang F, Zhang J (2001) Carbohydr Res 334:323

    Article  CAS  Google Scholar 

  21. Liu HM, Zhang F, Zhang J, Li S (2003) Carbohydr Res 338:1737

    Article  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful to the National Natural Science Foundation of China (No. 20972142, 20972130, 20732004), the State Key Laboratory of Bio-organic and Natural Products Chemistry, CAS (08417) for financial support.

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Authors and Affiliations

  1. Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry, Phosphorus Chemical Engineering Research Center of Henan Province, Zhengzhou University, 450052, Zhengzhou, People’s Republic of China

    Hong Liu, Fuyi Zhang, Jin-Peng Li, Xuebin Yan & Yu-Fen Zhao

  2. School of Pharmaceutical Sciences, Zhengzhou University, 100 Science Road, 450001, Zhengzhou, People’s Republic of China

    Hong-Min Liu

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  1. Hong Liu
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  2. Fuyi Zhang
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  3. Jin-Peng Li
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Correspondence to Fuyi Zhang or Yu-Fen Zhao.

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Liu, H., Zhang, F., Li, JP. et al. Novel Methyl 4,6-O-benzylidene-3-ketoglucopyranosid-fused γ-lactam: Synthesis and Crystal Structure. J Chem Crystallogr 41, 1228–1231 (2011). https://doi.org/10.1007/s10870-011-0079-6

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