Use of 1,3-dibenzyl-dihydrouracil in the chain extension of 2,3-O-isopropylidene-D-glyceraldehyde

Tetrahedron Letters

Volumn 44, Issue 4, 2003, Pages 671-675

  Ulgheri, Fausta ^a   Bacsa, John ^b   Nassimbeni, Luigi ^b   Spanu, Pietro ^a  

^a CNR Consiglio Nazionale delle Ricerche   (Italy)

^b UNIVERSITY OF CAPE TOWN   (South Africa)

Author keywords

Dihydropyrimidin 2,4 dione; Dihydrouracil; Glyceraldehyde

Indexed keywords

1,3 DIBENZYL DIHYDROURACIL; 2,3 O ISOPROPYLIDENE DEXTRO GLYCERALDEHYDE; 5 TRIHYDROXYPROPYL DIHYDROURACIL; DIHYDROURACIL; GLYCERALDEHYDE; LEWIS ACID; POLYOL; SOLVENT; UNCLASSIFIED DRUG; UREIDOPOLYOL;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; EPIMER; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 0037454978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02701-6     Document Type: Article

References (59)

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3. For a review, see: (a) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 1677-1716; (b) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629; (c) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 1929-1972; (d) Battistini, L.; Casiraghi, G.; Rassu, G.; Zanardi, F. Chem. Soc. Rev. 2000, 29, 109-118. For same references: (a) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807-5824; (b) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760-3763; (c) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 3237-3243; (d) Spanu, P.; Rassu, G.; Ulgheri, F.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron 1996, 52, 4829-4838; (e) Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513-4517.
4. For a review, see: (a) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 1677-1716; (b) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629; (c) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 1929-1972; (d) Battistini, L.; Casiraghi, G.; Rassu, G.; Zanardi, F. Chem. Soc. Rev. 2000, 29, 109-118. For same references: (a) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807-5824; (b) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760-3763; (c) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 3237-3243; (d) Spanu, P.; Rassu, G.; Ulgheri, F.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron 1996, 52, 4829-4838; (e) Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513-4517.
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6. For a review, see: (a) Casiraghi, G.; Zanardi, F.; Rassu, G.; Spanu, P. Chem. Rev. 1995, 1677-1716; (b) Casiraghi, G.; Rassu, G. Synthesis 1995, 607-629; (c) Casiraghi, G.; Zanardi, F.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 1929-1972; (d) Battistini, L.; Casiraghi, G.; Rassu, G.; Zanardi, F. Chem. Soc. Rev. 2000, 29, 109-118. For same references: (a) Casiraghi, G.; Colombo, L.; Rassu, G.; Spanu, P.; Gasparri Fava, G.; Ferrari Belicchi, M. Tetrahedron 1990, 46, 5807-5824; (b) Casiraghi, G.; Rassu, G.; Spanu, P.; Pinna, L. J. Org. Chem. 1992, 57, 3760-3763; (c) Spanu, P.; Rassu, G.; Pinna, L.; Battistini, L.; Casiraghi, G. Tetrahedron: Asymmetry 1997, 8, 3237-3243; (d) Spanu, P.; Rassu, G.; Ulgheri, F.; Zanardi, F.; Battistini, L.; Casiraghi, G. Tetrahedron 1996, 52, 4829-4838; (e) Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513-4517.
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41. A lithiated DHU derivative has been used as an 'amide α-anion' for the synthesis of 5-acyl-uridines nucleoside analogues. Hiroyuki, H.; Hiromichi, T.; Tadashi, M. Chem. Pharm. Bull. 1982, 30, 4589-4592. 5-C-Glycosyl uracil derivatives have been synthesized as nucleoside analogues via addition of 5-lithio uracil to aldehydo sugars. (a) Lerch, U.; Burdon, M. G.; Moffatt, J. G. J. Org. Chem. 1971, 36, 1507-1513; (b) Asbun, W.; Binkley, S. B. J. Org. Chem. 1966, 31, 2215-2219.
42. For some examples of bioactive glycosyl ureido derivatives, see: (a) Velazquez, S.; Chamorro, C.; Perez-Perez, M.-J.; Alvarez, R.; Jimeno, M.-L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.-J. J. Med. Chem. 1998, 41, 4636-4647; (b) Diaz Perez, V. M.; Ortiz Mellet, C.; Fuentes, J.; Garcia Fernandez, J. M. Carbohydr. Res. 2000, 326, 161-175. For some examples of the use of glycosyl ureido derivatives for the synthesis of bioactive molecules see: (a) Garcia-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 7604-7614; (b) Piekarska-Bartoszewicz, B.; Temeriusz, A. Carbohydr. Res. 1990, 203, 302-307; (c) Avalos Gonzalez M.; Cintas Moreno, P.; Gomez Monterrey, I. M.; Jimenez Requejo, J. L.; Palacios Albarran, J. C.; Rebolledo Vicente, F. Carbohydr. Res. 1990, 197, 310-317.
43. For some examples of bioactive glycosyl ureido derivatives, see: (a) Velazquez, S.; Chamorro, C.; Perez-Perez, M.-J.; Alvarez, R.; Jimeno, M.-L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.-J. J. Med. Chem. 1998, 41, 4636-4647; (b) Diaz Perez, V. M.; Ortiz Mellet, C.; Fuentes, J.; Garcia Fernandez, J. M. Carbohydr. Res. 2000, 326, 161-175. For some examples of the use of glycosyl ureido derivatives for the synthesis of bioactive molecules see: (a) Garcia-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 7604-7614; (b) Piekarska-Bartoszewicz, B.; Temeriusz, A. Carbohydr. Res. 1990, 203, 302-307; (c) Avalos Gonzalez M.; Cintas Moreno, P.; Gomez Monterrey, I. M.; Jimenez Requejo, J. L.; Palacios Albarran, J. C.; Rebolledo Vicente, F. Carbohydr. Res. 1990, 197, 310-317.
44. For some examples of bioactive glycosyl ureido derivatives, see: (a) Velazquez, S.; Chamorro, C.; Perez-Perez, M.-J.; Alvarez, R.; Jimeno, M.-L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.-J. J. Med. Chem. 1998, 41, 4636-4647; (b) Diaz Perez, V. M.; Ortiz Mellet, C.; Fuentes, J.; Garcia Fernandez, J. M. Carbohydr. Res. 2000, 326, 161-175. For some examples of the use of glycosyl ureido derivatives for the synthesis of bioactive molecules see: (a) Garcia-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 7604-7614; (b) Piekarska-Bartoszewicz, B.; Temeriusz, A. Carbohydr. Res. 1990, 203, 302-307; (c) Avalos Gonzalez M.; Cintas Moreno, P.; Gomez Monterrey, I. M.; Jimenez Requejo, J. L.; Palacios Albarran, J. C.; Rebolledo Vicente, F. Carbohydr. Res. 1990, 197, 310-317.
45. For some examples of bioactive glycosyl ureido derivatives, see: (a) Velazquez, S.; Chamorro, C.; Perez-Perez, M.-J.; Alvarez, R.; Jimeno, M.-L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.-J. J. Med. Chem. 1998, 41, 4636-4647; (b) Diaz Perez, V. M.; Ortiz Mellet, C.; Fuentes, J.; Garcia Fernandez, J. M. Carbohydr. Res. 2000, 326, 161-175. For some examples of the use of glycosyl ureido derivatives for the synthesis of bioactive molecules see: (a) Garcia-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 7604-7614; (b) Piekarska-Bartoszewicz, B.; Temeriusz, A. Carbohydr. Res. 1990, 203, 302-307; (c) Avalos Gonzalez M.; Cintas Moreno, P.; Gomez Monterrey, I. M.; Jimenez Requejo, J. L.; Palacios Albarran, J. C.; Rebolledo Vicente, F. Carbohydr. Res. 1990, 197, 310-317.
46. For some examples of bioactive glycosyl ureido derivatives, see: (a) Velazquez, S.; Chamorro, C.; Perez-Perez, M.-J.; Alvarez, R.; Jimeno, M.-L.; Martin-Domenech, A.; Perez, C.; Gago, F.; De Clercq, E.; Balzarini, J.; San-Felix, A.; Camarasa, M.-J. J. Med. Chem. 1998, 41, 4636-4647; (b) Diaz Perez, V. M.; Ortiz Mellet, C.; Fuentes, J.; Garcia Fernandez, J. M. Carbohydr. Res. 2000, 326, 161-175. For some examples of the use of glycosyl ureido derivatives for the synthesis of bioactive molecules see: (a) Garcia-Moreno, M. I.; Benito, J. M.; Ortiz Mellet, C.; Garcia Fernandez, J. M. J. Org. Chem. 2001, 66, 7604-7614; (b) Piekarska-Bartoszewicz, B.; Temeriusz, A. Carbohydr. Res. 1990, 203, 302-307; (c) Avalos Gonzalez M.; Cintas Moreno, P.; Gomez Monterrey, I. M.; Jimenez Requejo, J. L.; Palacios Albarran, J. C.; Rebolledo Vicente, F. Carbohydr. Res. 1990, 197, 310-317.
47. 3) δ 168.9, 153.8, 137.8, 136.3, 128.8, 128.6, 128.3, 127.9, 127.8, 127.3, 51.6, 43.9, 41.8, 31.7. White solid, mp 81-83°C.
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49. 3).
50. Nucleophilic addition of organometals to acetonide-protected glyceraldehyde generally exhibits anti diastereoselectivity rationalized by a Felkin-Anh or a Felkin-Anh β-chelate transition state: (a) Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488; (b) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E-21, pp. 1220-1235 and references cited therein.
51. Nucleophilic addition of organometals to acetonide-protected glyceraldehyde generally exhibits anti diastereoselectivity rationalized by a Felkin-Anh or a Felkin-Anh β-chelate transition state: (a) Jurczak, J.; Pikul, S.; Bauer, T. Tetrahedron 1986, 42, 447-488; (b) Devant, R. M.; Radunz, H.-E. Formation of C-C Bonds by Addition to Carbonyl Groups; Houben-Weyl, Georg Thieme: Stuttgart/New York, 1995; E-21, pp. 1220-1235 and references cited therein.
52. The formation of an ate complex or the transmetallation of the lithium enolate to Sn(IV) enolate can be considered.
53. Aldol reactions between α-chiral aldehydes and E(O)-enolates preferentially give the Felkin-type adduct by abiding both Felkin-Anh rule and the Zimmerman-Traxler model: (a) Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223; (b) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157; (c) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
54. Aldol reactions between α-chiral aldehydes and E(O)-enolates preferentially give the Felkin-type adduct by abiding both Felkin-Anh rule and the Zimmerman-Traxler model: (a) Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223; (b) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157; (c) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
55. Aldol reactions between α-chiral aldehydes and E(O)-enolates preferentially give the Felkin-type adduct by abiding both Felkin-Anh rule and the Zimmerman-Traxler model: (a) Mengel, A.; Reiser, O. Chem. Rev. 1999, 99, 1191-1223; (b) Roush, W. R. J. Org. Chem. 1991, 56, 4151-4157; (c) Gennari, C.; Vieth, S.; Comotti, A.; Vulpetti, A.; Goodman, J. M.; Paterson, I. Tetrahedron 1992, 48, 4439-4458.
56. Only 3% of epimerization was observed for the compound 4 in the same reaction condition.
57. 4 (6 equiv.) in THF we obtained only the product 9.
58. 3).
59. Crystallographic data for this structure have been deposited with the Cambridge Crystallographic Data centre as supplementary publication no. CCDC 193684. Copies of the data can be obtained free of charge on application to CCDC 12 Union Road, Cambridge CB21EZ (Fax: (+44) 1223-336-036. E-mail: deposit@ccdc.cam.ac.uk).