S. Henkel, M. Kleban and V. Jäger

Zeitschrift für Kristallographie - New Crystal Structures 212, 5 3 - 5 4

© by R. Oldenbourg Verlag, München 1997

5 3

C r y s t a l s t r u c t u r e o f ( 3 a / ? , 4 / ? , 5 S , 6 S ) - 4 , 5 , 6 - t r i s - a c e t o x y - ( 3 , 3 a , 5 , 6 ) - t e t r a h y d r o - ( 4 / / ) - c y c l o p e n t ( c ) i s o x a z o l e , C 1 2 H 1 5 N O 7

S. Henkel, M. Kleban and V. Jäger

Universität Stuttgart. Institut für Organische Chemie. Pfaffenwaldring 55, D-70569 Stuttgart, Germany Received June 5. 1996. CSD-No. 402504

32 Table 1. Parameters used for the X-ray data collection

Source of material: The title compound has been obtained by intramolecular nitrile oxide cycloaddition starting with the oxime of 2,3,4-tri-0-acetyl-D-jry/o-5-hexenose (see refs. 1, 2). Flash chromatography on silica and crystallisation from ethyl aceta- te/heptane gave the isoxazoline in the form of colorless crystals in 73 % yield. The title compound is related to several other derivatives that served as precursors for novel glycosidase inhi- bitors (see ref. 3).

C12H15NO7,

Crystal: colorless prism, size 0.6 χ 0.75 χ 1.75 mm Wavelength: Mo Ka radiation (0.71073 Â)

μ : 1.11 cm"1

Diffractometer: Nicolet P3

Scan mode: Wyckoff

Τ measurement'· 293 Κ

20max: 55°

N(hkl)um<¡ue: 1841 Criterion for /<>: / o > 2 σ( / ο )

Wj>aram)refine¡r. 181

Program: SHELXL-93

Table 2. Final atomic coordinates and displacement parameters (in Â2)

Atom Site X y ζ U,so

H(3A) 4a 0.4864(8) 0.0253(3) 0.2041(3) 0.076 H(3B) 4a 0.6068(8) 0.1121(3) 0.1651(3) 0.076 H(3A1) 4a 0.1611(7) 0.1062(3) 0.2381(2) 0.054 H(4) 4a 0.3451(6) 0.2457(3) 0.1381(2) 0.050 H(5) 4a -0.0735(6) 0.2724(2) 0.2275(2) 0.052 H(6) 4a 0.3439(7) 0.3501(3) 0.2898(2) 0.059 H(9A) 4a -0.152(2) 0.2910(6) 0.4620(3) 0.185 H(9B) 4a -0.329(2) 0.3679(6) 0.4339(3) 0.185 H(9C) 4a -0.114(2) 0.3943(6) 0.4868(3) 0.185 H(12A) 4a 0.063(1) 0.5155(3) 0.1099(2) 0.096 H(I2B) 4a -0.171(1) 0.5555(3) 0.1468(2) 0.096 H(12C) 4a -0.187(1) 0.4970(3) 0.0719(2) 0.096 H(15A) 4a -0.2470(9) 0.1347(4) 0.0237(2) 0.103 H(15B) 4a -0.1100(9) 0.0434(4) 0.0027(2) 0.103 H(15C) 4a -0.0759(9) 0.1327(4) -0.0468(2) 0.103

Table 3. Final atomic coordinates and displacement parameters (in À2)

Atom Site χ y ζ U11 t/22 í/33 f/12 C/13 ί/23 N(l) 4a 0.5777(7) 0.1894(3) 0.3126(2) 0.049(2) 0.076(2) 0.071(2) -0.003(2) -0.013(2) 0.011(2) 0(2) 4a 0.6616(6) 0.1074(3) 0.2779(2) 0.054(2) 0.083(2) 0.096(2) 0.019(2) -0.018(2) 0.009(2) C(3) 4a 0.5216(8) 0.0908(3) 0.2098(3) 0.051(2) 0.066(3) 0.073(3) 0.015(2) -0.004(2) 0.005(2) C(3A) 4a 0.2934(7) 0.1460(3) 0.2215(2) 0.035(2) 0.048(2) 0.051(2) -0.002(2) 0.000(2) 0.006(2) C(4) 4a 0.2085(6) 0.2190(3) 0.1653(2) 0.031(2) 0.046(2) 0.047(2) -0.001(2) 0.002(2) 0.002(2) C(5) 4a 0.0905(6) 0.2919(2) 0.2155(2) 0.035(2) 0.045(2) 0.051(2) -0.002(2) 0.005(2) 0.000(2) C(6) 4a 0.2379(7) 0.2960(3) 0.2889(2) 0.045(2) 0.053(2) 0.050(2) -0.009(2) 0.002(2) -0.001(2) C(6A) 4a 0.3753(7) 0.2085(3) 0.2838(2) 0.043(2) 0.054(2) 0.047(2) -0.007(2) -0.001(2) 0.009(2) 0(7) 4a 0.0899(7) 0.2916(2) 0.3561(2) 0.076(2) 0.065(2) 0.055(2) -0.009(2) 0.015(2) -0.010(1) C(8) 4a -0.013(1) 0.3704(5) 0.3786(3) 0.105(5) 0.096(4) 0.073(3) -0.009(4) 0.025(4) -0.025(3) 0(8) 4a 0.011(1) 0.4420(3) 0.3449(3) 0.197(7) 0.078(3) 0.127(4) 0.021(3) 0.062(5) -0.001(3) C( 9) 4a -0.166(2) 0.3545(6) 0.4463(3) 0.149(7) 0.123(5) 0.097(5) 0.001(6) 0.061(5) -0.034(4) O(10) 4a 0.0836(5) 0.3782(2) 0.1757(2) 0.045(1) 0.045(1) 0.066(2) 0.006(1) 0.004(1) 0.005(1)

54

Table 3. (Continued)

Atom Site X y z UM Un I/33 UM t/13 Uiì

C(ll) 4a -0.1306(9) 0.4190(3) 0.1645(2) 0.057(2) 0.061(2) 0.048(2) 0.015(2) -0.002(2) -0.004(2) CHID 4a -0.3124(6) 0.3853(4) 0.1861(3) 0.048(2) 0.125(3) 0.131(4) 0.026(2) 0.015(2) 0.042(3) C(12) 4a -0.104(1) 0.5041(3) 0.1193(2) 0.079(3) 0.060(2) 0.052(2) 0.021(3) -0.014(3) -0.008(2) 0(13) 4a 0.0287(5) 0.1875(2) 0.1124(1) 0.038(1) 0.061(2) 0.048(1) 0.006(1) -0.003(1) -0.006(1) C(14) 4a 0.1030(8) 0.1386(3) 0.0527(2) 0.047(2) 0.068(3) 0.050(2) 0.000(2) 0.005(2) -0.007(2) 0(14) 4a 0.3071(6) 0.1191(4) 0.0431(2) 0.046(2) 0.151(4) 0.091(3) 0.005(2) 0.008(2) -0.059(3) C(I5) 4a -0.1004(9) 0.1098(4) 0.0037(2) 0.059(2) 0.099(3) 0.049(2) 0.001(3) -0.007(2) -0.015(2)

Acknowledgments. We want to thank the Landesgraduiertenfördening Baden-

References

the Volkswagen-Stiftung, Hannover, for financial support. 1. Kleban, M.: Diastereoselektive Synthese von Aminocyclopentanpolyolen - "Desoxapyranosylamine" als neue Klasse von Glykosidase-Inhibitoren.

Dissertation, Universität Stuttgart, Germany 19%.

2. Fürstner, A: Jumbam, D.: Teslic, J.: Weidmann, H.: Metal-Graphite Reagents in Carbohydrate Chemistry. 8. The Scope and Limitations of the Use of Zinc/Silver-Graphite in the Synthesis of Carbohydrate-Derived Substituted Hex-S-enals and Pent-4-enals. J. Org. Chem. 56(1991) 2213- 2217.

3. Kleban, M.: Picasso, S.; Vogel, P.; Jäger, V.: Amino-hydroxymethyl-cy- clopentanetriols: an Emerging Class of Potent Glycosidase Inhibitors.

Synthesis and Evaluation of Mannoside Analogues. J. Chem. S oc. Chem.

Commun., submitted.

4. Sheldrick, G. M.: SHELXL-93, Program for the refinement of crystal structures. University of Göttingen, Germany 1993.