Crystal Structure Analysis of 2,3,4-Tri-O-acetyl-a-methyl-D-glucopyranoside

Xiao-Li Zhen; Zhen Zhou; Jian-Rong Han; Xia Tian; Shouxin Liu

doi:10.14233/ajchem.2015.17028

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Issue Published : January 10, 2015

This work is licensed under a Creative Commons Attribution 4.0 International License.

Crystal Structure Analysis of 2,3,4-Tri-O-acetyl-a-methyl-D-glucopyranoside

https://doi.org/10.14233/ajchem.2015.17028

Xiao-Li Zhen

College of Sciences, Hebei University of Science and Technology, Shijiazhuang 050018, P.R. China

Zhen Zhou

College of Sciences, Hebei University of Science and Technology, Shijiazhuang 050018, P.R. China

Jian-Rong Han

College of Sciences, Hebei University of Science and Technology, Shijiazhuang 050018, P.R. China

Xia Tian

College of Sciences, Hebei University of Science and Technology, Shijiazhuang 050018, P.R. China

Shouxin Liu

College of Chemical and Pharmaceutical Engineering, Hebei University of Science and Technology, Shijiazhuang 050018, P.R. China

Corresponding Author(s) : Jian-Rong Han

han_jianrong@126.com; jrhan@eyou.com

Asian Journal of Chemistry, Vol. 27 No. 2 (2015): Vol 27 Issue 2
Article Published : January 10, 2015

Abstract

2,3,4-Tri-O-acetyl-a-methyl-D-glucopyranoside (F.W. 319.28) was synthesized, characterized by ¹H NMR, confirmed by X-ray crystal structure analysis. This compound crystallizes in monoclinic class under the space group orthorhombic P2(1)2(1)2(1) with cell parameters a = 9.0312(18) Å, b = 11.731(2) Å, c = 15.139(3) Å; Z = 4. The structure exhibits inter-molecular hydrogen bonds of the type O-H---O, C-H---O.

Keywords

a-Methyl-D-glucopyranoside Protection Synthesis Crystal structure Hydrogen bond

Zhen, X.-L., Zhou, Z., Han, J.-R., Tian, X., & Liu, S. (2015). Crystal Structure Analysis of 2,3,4-Tri-O-acetyl-a-methyl-D-glucopyranoside. Asian Journal of Chemistry, 27(2), 552–554. https://doi.org/10.14233/ajchem.2015.17028

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References

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References

R.A. Dwek, Chem. Rev., 96, 683 (1996); doi:10.1021/cr940283b.

E. Walker-Nasir, A. Kaleem, D.C. Hoessli, A. Khurshid and B.S.P. Nasir-ud-Din, Curr. Org. Chem., 12, 940 (2008); doi:10.2174/138527208784892213.

H.E. Murrey and L.C. Hsieh-wilson, Chem. Rev., 108, 1708 (2008); doi:10.1021/cr078215f.

K. Toshima and K. Tatsuta, Chem. Rev., 93, 1503 (1993); doi:10.1021/cr00020a006.

K.C. Nicolaou and H.J. Mitchell, Angew. Chem. Int. Ed., 40, 1576 (2001); doi:10.1002/1521-3773(20010504)40:9<1576::AID-ANIE15760>3.0.CO;2-G.

A.V. Demchenko, Synlett, 1225 (2003); doi:10.1055/s-2003-40349.

B.G. Davis, J. Chem. Soc., Perkin Trans. I, 2137 (2000); doi:10.1039/a809774g.

A.R. Vaino and W.A. Szarek, Chem. Commun., 2351 (1996); doi:10.1039/cc9960002351.

R. Stiller and J. Thiem, in eds.: H. Ogura, A. Hasegawa and T. Suami, Carbohydrates: Synthetic Methods and Applications in Medicinal Chemistry, John Wiley & Sons, New York, p. 177 (1992).

M. Terreni, R. Salvetti, L. Linati, R. Fernandez-Lafuente, G. Fernández-Lorente, A. Bastida and J.M. Guisan, Carbohydr. Res., 337, 1615 (2002); doi:10.1016/S0008-6215(02)00113-1.

S. Koto, N. Morishima, Y. Kihara, H. Suzuki, S. Kosugi and S. Zen, Bull. Chem. Soc. Jpn., 56, 188 (1983); doi:10.1246/bcsj.56.188.

O. Kirk, M.W. Christensen, F. Beck and T. Damhus, Biocatal. Biotransform., 12, 91 (1995); doi:10.3109/10242429508998155.

A. Banaszek and Z. Ciunik, Tetrahedron Lett., 38, 273 (1997); doi:10.1016/S0040-4039(96)02290-3.

G. F. Springer, Mol. Immunol., 26, 1 (1989).

V. Kren and T. Rezanka, FEMS Microbiol. Rev., 32, 858 (2008); doi:10.1111/j.1574-6976.2008.00124.x.

M. Filice, J.M. Guisan and J.M. Palomo, Curr. Org. Chem., 14, 516 (2010); doi:10.2174/138527210790820276.

M.J. Kiefel, B. Beisner, S. Bennett, I.D. Holmes and M. von Itzstein, J. Med. Chem., 39, 1314 (1996); doi:10.1021/jm950611f.

X. l.Zhen, X. L. Li, X. Lu, J. Hebei Univ., 29, 164 (2009).

(a) G.M. Sheldrick, SHELXS-97. Program for Crystal Structure Solution, University of Gottingen, Germany (1997); (b) G.M. Sheldrick, SHELXL-97, Program for X-Ray Crystal Structure Refinement, University of Gottingen, Germany (1997).

Y.Y. Root, T.R. Wagner and P. Norris, Carbohydr. Res., 337, 2343 (2002); doi:10.1016/S0008-6215(02)00297-5.

D. Cremer and J.A. Pople, J. Am. Chem. Soc., 97, 1354 (1975); doi:10.1021/ja00839a011.

Issue

Vol. 27 No. 2 (2015): Vol 27 Issue 2

Crystal Structure Analysis of 2,3,4-Tri-O-acetyl-a-methyl-D-glucopyranoside

Corresponding Author(s) : Jian-Rong Han

Abstract

Keywords

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