2-Acetamido-N-benzyl-1,4-imino-1,2,4-tride­oxy-l-xylitol (N-benzyl-l-XYLNAc)

Jenkinson, S.F.; Crabtree, E.V.; Glawar, A.F.G.; Butters, T.D.; Fleet, G.W.J.; Watkin, D.J.

doi:10.1107/S1600536810014145

Volume 66
Part 5
Pages o1147-o1148
May 2010

Received 13 April 2010
Accepted 16 April 2010
Online 24 April 2010

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R = 0.051
wR = 0.130
Data-to-parameter ratio = 10.4
Details

2-Acetamido-N-benzyl-1,4-imino-1,2,4-trideoxy-L-xylitol (N-benzyl-L-XYLNAc)

Sarah. F. Jenkinson,^a ^* Elizabeth. V. Crabtree,^a Andreas. F. G. Glawar,^a Terry D. Butters,^b George. W. J. Fleet ^a and David. J. Watkin ^c

^aDepartment of Organic Chemistry, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England,^bOxford Glycobiology Institute, University of Oxford, South Parks Road, Oxford OX1 3QU, England, and ^cDepartment of Chemical Crystallography, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, England
Correspondence e-mail: sarah.jenkinson@chem.ox.ac.uk

X-ray crystallography defines the relative configuration at the three-stereogenic centres in the title compound N-benzyl-L-XYLNAc, C₁₄H₂₀N₂O₃. The five-membered pyrrolidine ring adopts an envelope conformation with the N atom lying out of the plane of the other four atoms. In the crystal structure, intermolecular O-HO, N-HO and O-HN hydrogen bonds link the molecules into chains along [100]. The carbonyl group O atom acts as an acceptor for a bifurcated hydrogen bond. The absolute configuration is determined by the use of L-glucuronolactone as the starting material for the synthesis.

Related literature

For iminosugars see: Asano et al. (2000); Watson et al. (2001). For the inhibition of hexosaminidases, see: Liu, Numa et al. (2004); Reese et al. (2007); Liu, Iqbal et al. (2004); Woynarowska et al. (1992). For piperidine hexosaminidase inhibitors, see: Tatsuta et al. (1997); Fleet et al. (1986, 1987); Steiner et al. (2009); Ho et al. (2010); For furanose hexosaminidase inhibitors, see: Usuki et al. (2009); Rountree et al. (2007, 2009); Boomkamp et al. (2010). For strategies for cancer treatment, see: Kato et al. (2010); Greco et al. (2009). For the use of glucuronolactone as a starting material for the synthesis of iminosugars, see: Best, Wang et al. (2010); Best, Chairatana et al. (2010).

Experimental

Crystal data

C₁₄H₂₀N₂O₃
M_r = 264.32
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.9731 (1) Å
b = 10.0145 (3) Å
c = 26.9297 (7) Å
V = 1341.18 (6) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 150 K
0.50 × 0.15 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) T_min = 0.77, T_max = 1.00
7494 measured reflections
1788 independent reflections
1471 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.130
S = 0.95
1788 reflections
172 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.46 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O15-H151O19ⁱ	0.85	1.94	2.790 (4)	173
N16-H161O19ⁱⁱ	0.89	2.19	3.041 (4)	159
O1-H11N4ⁱⁱ	0.85	2.29	3.121 (4)	167
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x+1, y, z.

Data collection: COLLECT (Nonius, 2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK and Görbitz (1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5029 ).

References

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organic compounds