A selective and operationally simple approach for removal of methoxy-, allyloxy-, and benzyloxycarbonyl groups from carbinols

Tetrahedron Letters

Volumn 50, Issue 50, 2009, Pages 7051-7054

  Adinolfi, Matteo ^a   Iadonisi, Alfonso ^a   Pastore, Antonello ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

Alkoxycarbonyl groups; Carbohydrates; Lithium iodide; Protecting groups

Indexed keywords

ACETIC ACID; CARBOHYDRATE DERIVATIVE; CARBONYL DERIVATIVE; LITHIUM DERIVATIVE; LITHIUM IODIDE; METHANOL DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; SEPARATION TECHNIQUE; STOICHIOMETRY; SYNTHESIS; TRANSESTERIFICATION;

EID: 70350518981     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.174     Document Type: Article

References (34)

1. For some examples:. Sridhar P.R., and Chandrasekaran S. Org. Lett. 4 (2002) 4731-4733
2. Morere A., Mouffouk F., Jeanjean A., Leydet A., and Montero J.L. Carbohydr. Res. 338 (2003) 2409-2412
3. Tanaka H., Amaya T., and Takahashi T. Tetrahedron Lett. 44 (2003) 3053-3057
4. Orgueira H.A., Bartolozzi A., Schell P., Litjens R.E.J.N., Palmacci E.R., and Seeberger P.H. Chem. Eur. J. 9 (2003) 140-169
5. Adinolfi M., Iadonisi A., Ravidà A., and Schiattarella M. Synlett (2004) 275-278
6. Ko K.S., Jaipuri F.A., and Pohl N.L. J. Am. Chem. Soc. 127 (2005) 13162-13163
7. de Oliveira R.N., Cottier L., Sinou D., and Srivastavab R.M. Tetrahedron 61 (2005) 8271-8281
8. Kim J.H., Yang H., Khot V., Whitfield D., and Boons G.-J. Eur. J. Org. Chem. (2006) 5007-5028
9. For a recent review:. Mohr J.T., and Stoltz B.M. Chem. Asian J. 2 (2007) 1476-1491
10. Poirier D., Berthiaume D., and Boivin R.P. Synlett (1999) 1423-1425
11. Berthiaume D., and Poirier D. Tetrahedron 56 (2000) 5995-6003
12. Wuts P.G.M., and Greene T.W. Greene's Protective Groups in Organic Synthesis (2007), Wiley & Sons
13. Adinolfi M., Iadonisi A., Pezzella A., and Ravidà A. Synlett (2005) 1848-1852
14. Adinolfi M., Barone G., Iadonisi A., and Guariniello L. Tetrahedron Lett. 41 (2000) 9305-9309
15. Adinolfi M., Barone G., Iadonisi A., Mangoni L., and Schiattarella M. Tetrahedron Lett. 42 (2001) 5967-5969
16. Adinolfi M., Barone G., Iadonisi A., and Schiattarella M. Org. Lett. 5 (2003) 987-989
17. For an application to a biologically relevant target:. Adinolfi M., Iadonisi A., Ravidà A., and Schiattarella M. J. Org. Chem. 70 (2005) 5316-5319
18. For a recent example of a sterically bulky participating groups for 1,2-trans glycosidations:. Szpilman A.M., and Carreira E.M. Org. Lett. 11 (2009) 1305-1307
19. For a recent report on the generation of saccharidic cyclic carbonates arising from participation effects:. Crich D., Hu T., and Cai F. J. Org. Chem. 73 (2008) 8942-8953
20. Bouzbouz S., and Kirschleger B. Synthesis (1994) 714-718
21. For some examples:. Mayato C., Dorta R.L., and Vazquez J.T. Tetrahedron Lett. 49 (2008) 1396-1398
22. Fisher J.W., and Trinkle K.L. Tetrahedron Lett. 35 (1994) 2505-2508
23. Biron E., and Kessler H. J. Org. Chem. 70 (2005) 5183-5189
24. For some examples:. Borch R.F., Grudzinskas C.V., Peterson D.A., and Weber L.D. J. Org. Chem. 37 (1972) 1141-1145
25. Wade J.J., Hegel R.F., and Toso C.B. J. Org. Chem. 44 (1979) 1811-1816
26. Magnus P., and Gallagher T. J. Chem. Soc., Chem. Commun. (1984) 389-390
27. Sun B., Srinivasan B., and Huang X. Chem. Eur. J. 14 (2008) 7072-7081
28. Haines A.H. Adv. Carbohydr. Chem. Biochem. 33 (1976) 11
29. For the use of N-methoxycarbonylated sugars in carbohydrate chemistry:. Yeung B.K.S., Adamski-Werner S.L., Bernard J.B., Poulenat G., and Petillo P.A. Org. Lett. 2 (2000) 3135-3138
30. Adinolfi M., Iadonisi A., and Ravidà A. Synlett (2006) 583-586
31. For the effect of the N-phtalimido group on regioselective glycosidations of glucosamine acceptors:. Ellervik U., and Magnusson G. J. Org. Chem. 63 (1998) 9314-9322
32. Bohn M.L., Colombo M.I., Pisano P.L., Stortz C.A., and Rùveda E.A. Carbohydr. Res. 342 (2007) 2522-2536
33. Adinolfi M., Iadonisi A., Ravidà A., and Valerio S. Tetrahedron Lett. 47 (2006) 2595-2599
34. Experimental procedure: The saccharidic compound (0.3 mmol) and LiI (120 mg, 0.9 mmol) were dissolved in pyridine (1.4 mL) and to the resulting solution was added acetic acid (90 μL, 1.5 mmol). The resulting mixture was refluxed for the times indicated on Table 1, and then the vessel was cooled to rt. The mixture was diluted with DCM and the organic phase was washed with water. The aqueous phase was re-extracted with DCM and ethyl acetate. The collected organic phases were dried and concentrated in vacuo to give a residue which was purified by silica gel flash chromatography (eluent: petroleum ether/ethyl acetate mixtures).