Synthesis of PI-88 analogue using novel O-glycosidation of exo-methylenesugars

Tetrahedron Letters

Volumn 46, Issue 17, 2005, Pages 3033-3036

  Namme, Rie ^a   Mitsugi, Takashi ^a   Takahashi, Hideyo ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

1 exo Methylenesugar; Heparanase inhibitor; O Glycosidation; PI 88

Indexed keywords

BENZYL DERIVATIVE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; ENZYME INHIBITOR; MESYLIC ACID; PHOSPHOMANNOPENTAOSE SULFATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; GLYCOSIDATION; QUANTUM YIELD; STEREOCHEMISTRY;

EID: 15944393889     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.03.016     Document Type: Article

References (16)

1. D.R. Coombe, C.R. Parish, I.A. Ramshaw, and J.M. Anowden Int. J. Cancer 39 1987 82
2. C.R. Parish, C. Freeman, K.J. Brown, D.J. Francis, and W.B. Cowden Cancer Res. 59 1999 3433
3. For a review, see: L.M. Khachigian, and C.R. Parish Cardiovasc. Drug Rev. 22 2004 1 PI-88 has received orphan drug designation from FDA
4. X.L. Li, H. Ohtake, H. Takahashi, and S. Ikegami Tetrahedron 57 2001 4283
5. X.L. Li, H. Ohtake, H. Takahashi, and S. Ikegami Synlett 2001 1885
6. C.-F. Chang, W.-B. Yang, C.-C. Chang, and C.-H. Lin Tetrahedron Lett. 43 2002 6515
7. H.-C. Lin, W.-B. Yang, Y.-F. Gu, C.-Y. Chen, C.-Y. Wu, and C.-H. Lin Org. Lett. 5 2003 1087
8. P.A. Colinas, A. Lieberknecht, and R.D. Bravo Tetrahedron Lett. 43 2002 9065
9. P.A. Colinas, A. Ponzinibbio, A. Lieberknecht, and R.D. Bravo Tetrahedron Lett. 44 2003 7985
10. Before our report, there were two papers on the O-glycosidation of 1-exo-methylenesugars. Enzymatic reaction, see: P. Schlesselmann, H. Fritz, J. Lehmann, T. Uchiyama, C.F. Brewer, and E.J. Hehre Biochemistry 21 1982 6606
11. the reaction promoted by iodonium ion, see: D. Noort, G.H. Veeneman, G.-J.P.H. Boons, G.A. van der Marel, G.J. Mulder, and J.H. van Boom Synlett 1990 205
12. Cleavage of a PMB ether under acidic conditions has been reported: T.W. Greene, and P.G.M. Wuts Protective Groups in Organic Synthesis 3rd ed. 1999 John Wiley & Sons New York
13. 3)
14. N.A. Petasis, and E.I. Bzowej J. Am. Chem. Soc. 112 1990 6392
15. N.A. Petasis, and S.-P. Lu Tetrahedron Lett. 36 1995 2393
16. 2, see: J.F. Payack, D.L. Hughes, D. Cai, I.F. Cottrell, and T.R. Verhoeven Org. Prep. Proced. Int. 27 1995 707