Glycono-1,3-lactams, Xylo Series: Stereoselective Access by [2+2] Cycloaddition, Exploratory Transformations, and Discovery of a New, Highly Selective Inhibitor of Glucoamylases

Synlett

Volumn 1997, Issue 3, 1997, Pages 295-297

  Krämer, Bernd ^a   Franz, Thomas ^a   Picasso, Sylviane ^b   Pruschek, Petra ^a,b   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

^b UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0042468658     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-759     Document Type: Article

References (79)

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48. 1H NMR spectrum; cf. Ref. 11c-f.
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52. D +8.5 (c= 1.34).
53. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
54. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
55. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
56. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
57. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
58. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
59. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
60. For uses of glyceraldehyde acetonide imines in [2+2] cyclo-additions see, e.g.: (a) Hubschwerlen, C.; Schmid, G. Helv. Chim. Acta 1983, 66, 2206. (b) Hubschwerlen, C. Synthesis 1986, 962. (c) Bose, A. K.; Manhas, M. S.; Van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hedge, V. R.; Krishnan, L. Tetrahedron Lett. 1985, 26, 33. (d) Bose, A. K.; Hedge, V. R.; Wagle, D. R.; Bari, S. S.; Manhas, M. S. J. Chem. Soc., Chem. Commun. 1986, 161. (e) Palomo, C.; Cossio, F. P.; Ontoria, J. M.; Odriozola, J. M. Tetrahedron Lett. 1991, 32, 3105. (f) Welch, J. T.; Araki, K.; Kawecki, R.; Wichtowski, J. A. J. Org. Chem. 1993, 58, 2454. (g) Niu, C.; Miller, M. J. Tetrahedron Lett. 1995, 36, 497. (h) See Ref. 18.
61. The relative configurations of the compounds 11a, 17 and 22a were secured by X-ray crystallographic examination: 11a, CSD No. 402600: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. -17, CSD No. 402601: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. - 22a, CSD No. 402692: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., submitted. Cf. X-ray structure of a related β-lactam derived from 9: CSD No. 402716 Peters, E. M.; Peters, K.; von Schnering, H. G.; Franz, T.; Jäger, V. Z. Kristallogr., submitted.
62. The relative configurations of the compounds 11a, 17 and 22a were secured by X-ray crystallographic examination: 11a, CSD No. 402600: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. -17, CSD No. 402601: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. - 22a, CSD No. 402692: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., submitted. Cf. X-ray structure of a related β-lactam derived from 9: CSD No. 402716 Peters, E. M.; Peters, K.; von Schnering, H. G.; Franz, T.; Jäger, V. Z. Kristallogr., submitted.
63. The relative configurations of the compounds 11a, 17 and 22a were secured by X-ray crystallographic examination: 11a, CSD No. 402600: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. -17, CSD No. 402601: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. - 22a, CSD No. 402692: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., submitted. Cf. X-ray structure of a related β-lactam derived from 9: CSD No. 402716 Peters, E. M.; Peters, K.; von Schnering, H. G.; Franz, T.; Jäger, V. Z. Kristallogr., submitted.
64. The relative configurations of the compounds 11a, 17 and 22a were secured by X-ray crystallographic examination: 11a, CSD No. 402600: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. -17, CSD No. 402601: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., in print. - 22a, CSD No. 402692: Henkel, S.; Krämer, B.; Jäger, V. Z. Kristallogr., submitted. Cf. X-ray structure of a related β-lactam derived from 9: CSD No. 402716 Peters, E. M.; Peters, K.; von Schnering, H. G.; Franz, T.; Jäger, V. Z. Kristallogr., submitted.
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