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Volume 69 
Part 6 
Page o917  
June 2013  

Received 26 March 2013
Accepted 8 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
Disorder in main residue
R = 0.055
wR = 0.149
Data-to-parameter ratio = 11.1
Details
Open access

2-Acetylamino-1,3,4,6-tetra-O-(trimethylsilyl)-2-deoxy-[alpha]-D-glucopyranose

aDepartment of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, People's Republic of China, and bZhejiang Provincial Key Lab for Chem. & Bio. Processing Technology of Farm Produce, Hangzhou, Zhejiang 310027, People's Republic of China
Correspondence e-mail: hnzzcyl@hotmail.com

The title compound, C20H47NO6Si4, was synthesized by per-O-trimethylsilylation of N-acetyl-D-glucosamine using chlorotrimethylsilane in the presence of hexamethyldisiloxane. The trimethylsilyl group and acetamido group are located on the same side of the pyran ring, showing an [alpha]-configuration glycoside. One of the trimethylsilyl groups is disordered over two orientations, with site-occupancy factors of 0.625 (9) and 0.375 (9). In the crystal, N-H...O hydrogen bonds link the molecules into supramolecular chains along the a-axis direction.

Related literature

For background to the title compound, see: Augé et al. (1985[Augé, C., David, S., Gautheron, C. & Veyrières, A. (1985). Tetrahedron Lett. 26, 2439-2440.]); Ronnow et al. (1994[Ronnow, T. E. C. L., Meldal, M. & Bock, K. (1994). Carbohydr. Res. 260, 323-328.]); Du & Gervais-Hague (2005[Du, W. & Gervais-Hague, J. (2005). Org. Lett. 7, 2063-2065.]); Wang et al. (2007[Wang, C.-C., Lee, J.-C., Luo, S.-Y., Kulkarni, S.-S., Huang, Y.-W., Lee, C.-C., Chang, K.-L. & Hung, S.-C. (2007). Nature, 446, 896-899.]); Witschi & Gervais-Hague (2010[Witschi, M. A. & Gervais-Hague, J. (2010). Org. Lett. 12, 4312-4315.]). For related structures, see: Odinokov et al. (2002[Odinokov, V. N., Savchenko, R. G., Nazmeeva, S. R., Galyautdinov, I. V. & Khalilov, L. M. (2002). Russ. Chem. Bull. 51, 1937-1939.]); Hu et al. (2011[Hu, Y.-P., Lin, S.-Y., Huang, C.-Y., Zulueta, M. M., Liu, J.-Y., Chang, W. & Hung, S.-C. (2011). Nat. Chem. 3, 557-563.]). For the synthesis, see: Loganathan & Trivedi (1987[Loganathan, D. & Trivedi, G. K. (1987). Carbohydr. Res. 162, 117-125.]); Jervis et al. (2010[Jervis, P. J., Veerapen, N., Bricard, G., Cox, L. R., Porcelli, S. A. & Besra, G. S. (2010). Bioorg. Med. Chem. Lett. 20, 3475-3478.]).

[Scheme 1]

Experimental

Crystal data
  • C20H47NO6Si4

  • Mr = 509.95

  • Orthorhombic, P 21 21 21

  • a = 9.4500 (7) Å

  • b = 12.8824 (9) Å

  • c = 27.295 (3) Å

  • V = 3322.9 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.38 × 0.20 × 0.19 mm

Data collection
  • Agilent Xcalibur (Atlas, Gemini ultra) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO, Agilent Technologies, Yarnton, England.]) Tmin = 0.926, Tmax = 0.962

  • 9896 measured reflections

  • 3438 independent reflections

  • 2105 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.149

  • S = 1.01

  • 3438 reflections

  • 309 parameters

  • 183 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O3i 0.86 2.03 2.855 (4) 160
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2].

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO, Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2199 ).


Acknowledgements

This work was supported financially by the National Science Foundation of China (No. 30870553) and the Key International S&T Cooperation Project, China (No. 2010DFA34370).

References

Agilent (2011). CrysAlis PRO, Agilent Technologies, Yarnton, England.
Augé, C., David, S., Gautheron, C. & Veyrières, A. (1985). Tetrahedron Lett. 26, 2439-2440.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Du, W. & Gervais-Hague, J. (2005). Org. Lett. 7, 2063-2065.  [ISI] [CrossRef] [PubMed] [ChemPort]
Hu, Y.-P., Lin, S.-Y., Huang, C.-Y., Zulueta, M. M., Liu, J.-Y., Chang, W. & Hung, S.-C. (2011). Nat. Chem. 3, 557-563.  [CrossRef] [ChemPort] [PubMed]
Jervis, P. J., Veerapen, N., Bricard, G., Cox, L. R., Porcelli, S. A. & Besra, G. S. (2010). Bioorg. Med. Chem. Lett. 20, 3475-3478.  [CrossRef] [ChemPort] [PubMed]
Loganathan, D. & Trivedi, G. K. (1987). Carbohydr. Res. 162, 117-125.  [CrossRef] [ChemPort] [ISI]
Odinokov, V. N., Savchenko, R. G., Nazmeeva, S. R., Galyautdinov, I. V. & Khalilov, L. M. (2002). Russ. Chem. Bull. 51, 1937-1939.  [ISI] [CrossRef] [ChemPort]
Ronnow, T. E. C. L., Meldal, M. & Bock, K. (1994). Carbohydr. Res. 260, 323-328.  [ChemPort] [PubMed] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Wang, C.-C., Lee, J.-C., Luo, S.-Y., Kulkarni, S.-S., Huang, Y.-W., Lee, C.-C., Chang, K.-L. & Hung, S.-C. (2007). Nature, 446, 896-899.  [ISI] [CrossRef] [PubMed] [ChemPort]
Witschi, M. A. & Gervais-Hague, J. (2010). Org. Lett. 12, 4312-4315.  [ISI] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o917  [ doi:10.1107/S160053681301266X ]

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