From sugars to carba-sugars

The Organic Chemistry of Sugars

Volumn , Issue , 2005, Pages 349-382

  Sollogoub, Matthieu ^a   Sinaÿ, Pierre ^a  

^a ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 85056047951     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/9781420027952     Document Type: Chapter

References (68)

1. McCasland, G E, Furuta, S, Durham, L J, Alicyclic carbohydrates. XXIX. The synthesis of a pseudohexose (2,3,4,5-tetrahydrocyclohexanemethanol), J. Org. Chem., 31, 1516-1521, 1966.
2. Suami, T, Ogawa, S, Chemistry of carba-sugars (pseudo-sugars) and their derivatives, Adv. Carbohydr. Chem. Biochem., 48, 21-90, 1990.
3. Le Merrer, Y, Gravier-Pelletier, C, Maton, W, Numa, W M, Depezay, J-C, A concise route to carbasugars, Synlett, 8, 1322-1324, 1999.
4. Ohtake, H, Li, X L, Shiro, M, Ikegami, S, A highly efficient and shortcut synthesis of cyclitol derivatives via spiro sugar ortho esters, Tetrahedron, 56, 7109-7122, 2000.
5. Miller, T W, Arison, B H, Albers-Schonberg, G, Isolation of a cyclitol antibiotic: 2,3,4,5-tetrahydroxycyclohexanemethanol, Biotech. Bioeng., 15, 1075-1080, 1973.
6. McCasland, G E, Furuta, S, Durham, L J, Alicyclic carbohydrates. XXIX. Epimerization of pseudo-alpha-DL-galactopyranose. Proton magnetic resonance studies, J. Org. Chem., 33, 2841-2847, 1968.
7. Ogawa, S, Maruyama, A, Odagiri, T, Yuasa, H, Hashimoto, H, Synthesis and biological evaluation of alpha-L-fucosidase inhibitors: 5a-carba-alpha-L-fucopyranosylamine and related compounds, Eur. J. Org. Chem., 5, 967-974, 2001.
8. Carpintero, M, Bastida, A, Garcia-Junceda, E, Jimenez-Barbero, J, Fernandez-Mayoralas, A, Synthesis of carba-and C-fucopyranosides and their evaluation as a-fucosidase inhibitors-analysis of an unusual conformation adopted by an amino-C-fucopyranoside, Eur. J. Org. Chem., 4, 4127-4135, 2001.
9. Suami, T, Ogawa, S, Toyokuni, T, Sweet tasting pseudo-sugars, Chem. Lett., 4, 611-612, 1983.
10. Ogawa, S, Uematsu, Y, Yoshida, S, Sasaki, N, Suami, T, Pseudo-sugars. 18. Synthesis and sweetness of pseudo-beta-D and L-fructopyranose, J. Carbohydr. Chem., 6, 471-478, 1987.
11. Kitaoka, M, Ogawa, S, Taniguchi, H, A cellobiose phosphorylase from cellvibrio-gilvus recognizes only the beta-D-form of 5a-carba-glucopyranose, Carbohydr. Res., 247, 355-359, 1993.
12. Callam, C S, Lowary, T L, Synthesis and conformational investigation of methyl 4a-carba-D-arabinofuranosides, J. Org. Chem., 66, 8961-8972, 2001.
13. Carpintero, M, Fernandez-Mayoralas, A, Jimenez-Barbero, J, The conformational behaviour of fucosyl and carbafucosyl mimetics in the free and in the protein-bound states, Eur. J. Org. Chem., 4, 681-689, 2001.
14. Ogawa, S, Sasaki, S, Tsunoda, H, Synthesis of carbocyclic analogs of the mannosyl trisaccharide-ether-linked and imino-linked methyl 3,6-bis(5a-carba-alpha-D-mannopyranosyl)-3,6-dideoxy-alpha-D-mannopyranosides, Carbohydr. Res., 274, 183-196, 1995.
15. 3 -a reactive acceptor analog for N-acetylglucosaminyltransferase-V, Carbohydr. Res., 271, 197-205, 1995.
16. Ogawa, S, Matsunaga, N, Li, H, Palcic, M M, Pseudosugars, 40-synthesis of ether-and iminolinked octyl N-acetyl-5a0-carba-beta-lactosaminides and-isolactosaminides: acceptor substrates for alpha-(1 !3/4)-fucosyltransferase, and enzymatic synthesis of 5a0-carbatrisaccharides, Eur. J. Org. Chem., 631-642, 1999.
17. Wilcox, C S, Gaudino, J J, New approaches to enzyme regulators. Synthesis and enzymological activity of carbocyclic analogues of D-fructofuranose and D-fructofuranose 6-phosphate, J. Am. Chem. Soc., 108, 3102-3104, 1986.
18. Fukusima, Y, Hayashi, M, Fujiwara, M, Miyagawa, T, Yoshikawa, G, Yano, T, Nakajima, H, Enzymatic synthesis of carbocyclic analogue of fructose 2,6-bisphosphate with 6-phosphofructo-2-kinase, Chem. Lett., 575-576, 1998.
19. Cai, S, Stroud, M R, Hakomori, S, Toyokuni, T, Synthesis of carbocyclic analogs of guanosine 50-(beta-L-fucopyranosyl diphosphate) (GDP-fucose) as potential inhibitors of fucosyltransferases, J. Org. Chem., 57, 6693-6696, 1992.
20. Yuasa, H, Palcic, M M, Hindsgaul, O, Synthesis of the carbocyclic analog of uridine 50-(alpha-D-galactopyranosyl diphosphate) (UDP-Gal) as an inhibitor of beta(1 !4)-galactosyltransferase, Can. J. Chem., 73, 2190-2195, 1995.
21. Ferrier, R J, Middleton, S, The conversion of carbohydrate-derivatives into functionalized cyclohexanes and cyclopentanes, Chem. Rev., 93, 2779-2831, 1993.
22. Ferrier, R J, Direct conversion of 5,6-unsaturated hexopyranosyl compounds to functionalized cyclohexanones, Top. Curr. Chem., 215, 277-291, 2001.
23. Dalko, P I, Sinaÿ, P, Recent advances in the conversion of carbohydrate furanosides and pyranosides into carbocycles, Angew. Chem. Int. Ed., 38, 773-777, 1999.
24. Suami, T, Tadano, K, Kameda, Y, Iimura, Y, Synthesis of optically-active pseudo-alpha-D-glucose and pseudo-beta-L-altrose, Chem. Lett., 1919-1922, 1984.
25. Tadano, K I, Kameda, Y, Iimura, Y, Suami, T, Syntheses of pseudo-alpha-D-glucopyranose and pseudo-beta-L-altropyranose from L-arabinose, J. Carbohydr. Chem., 6, 231-244, 1987.
26. Tadano, K, Maeda, H, Hoshino, M, Iimura, Y, Suami, T, A new transformation of aldose derived synthons to pseudo-hexopyranose or pseudo-pentofuranose derivatives, Chem. Lett., 1081-1084, 1986.
27. Tadano, K I, Maeda, H, Hoshino, M, Iimura, Y, Suami, T, A novel transformation of 4 aldoses to some optically pure pseudohexopyranoses and a pseudopentofuranose, carbocyclic analogs of hexopyranoses and pentofuranose-synthesis of derivatives of (1S,2S,3R,4S,5S)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes, (1S,2S,3R,4R,5S)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes, (1R,2R,3R,4R,5S)-2,3,4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes, (1S,2S,3R,4S,5R)-2,3, 4,5-tetrahydroxy-1-(hydroxymethyl)cyclohexanes and (1S,2S,3S,4S)-2,3,4-trihydroxy-1-(hydroxymethyl) cyclopentane, J. Org. Chem., 52, 1946-1956, 1987.
28. Yoshikawa, M, Cha, B C, Nakae, T, Kitagawa, I, Syntheses of pseudo-alpha-D-glucopyranose and pseudo-beta-L-idopyranose, two optically-active pseudo-hexopyranoses, from D-glucose by using stereoselective reductive deacetoxylation with sodium-borohydride and cyclitol formation from nitrofuranose as key reactions, Chem. Pharm. Bull., 36, 3714-3717, 1988.
29. Yoshikawa, M, Cha, B C, Okaichi, Y, Kitagawa, I, Synthesis of pseudo-alpha-D-arabinofuranose, pseudo-beta-D-arabinofuranose, and pseudo-beta-L-xylofuranose, three optically-active pseudopentofuranoses, from D-glucose, Chem. Pharm. Bull., 36, 3718-3721, 1988.
30. Yoshikawa, M, Murakami, N, Inoue, Y, Hatakeyama, S, Kitagawa, I, A new approach to the synthesis of optically-active pseudo-sugar and pseudo-nucleoside-syntheses of pseudo-alpha-D-arabinofuranose, (þ)-cyclaradine, and (þ)-1-pseudo-beta-D-arabinofuranosyluracil from D-arabinose, Chem. Pharm. Bull., 41, 636-638, 1993.
31. Paulsen, H, Vondeyn, W, Cyclitol reactions 13. Synthesis of pseudosugars from D-glucose by intramolecular Horner-Emmons olefination, Liebigs Ann. Chem., 2, 125-131, 1987.
32. Suami, T, Tadano, K, Ueno, Y, Fukabori, C, A novel synthesis of pseudo-alpha-L-altropyranose from D-glucose, Chem. Lett., 1557-1560, 1985.
33. Tadano, K, Ueno, Y, Fukabori, C, Hotta, Y, Suami, T, Construction of an optically-active 7-oxabicyclo(4.3.0)non-4-en-3-one skeleton from D-glucose, and its transformation to some pseudohexopyranoses, Bull. Chem. Soc. Jpn., 60, 1727-1739, 1987.
34. Rassu, G, Auzzas, L, Pinna, L, Battistini, L, Zanardi, F, Marzocchi, L, Acquotti, D, Casiraghi, G, Variable strategy toward carbasugars and relatives. 1. Stereocontrolled synthesis of pseudo-beta-Dgulopyranose, pseudo-beta-D-xylofuranose, (pseudo-beta-D-gulopyranosyl)amine, and (pseudo-beta-D-xylofuranosyl)amine, J. Org. Chem., 65(20), 6307-6318, 2000.
35. Zanardi, F, Battistini, L, Marzocchi, L, Acquotti, D, Rassu, G, Pinna, L, Auzzas, L, Zambrano, V, Casiraghi, G, Synthesis of a small repertoire of non-racemic 5a-carbahexopyranoses and 1-thio-5acarbahexopyranoses, Eur. J. Org. Chem., 1956-1965, 2002.
36. Rassu, G, Auzzas, L, Pinna, L, Zambrano, V, Battistini, L, Zanardi, F, Marzocchi, L, Acquotti, D, Casiraghi, G, Variable strategy toward carbasugars and relatives. 2. Diversity-based synthesis of beta-D-xylo, beta-D-ribo, beta-L-arabino, and beta-L-lyxo 4a-carbafuranoses and (4a-carbafuranosyl)thiols, J. Org. Chem., 66, 8070-8075, 2001.
37. Keck, G E, Kachensky, D F, Enholm, E J, Pseudomonic acid C from L-lyxose, J. Org. Chem., 50, 4317-4325, 1985.
38. Cheng, X H, Khan, N, Kumaran, G, Mootoo, D R, A convergent strategy for the synthesis of betacarba-galacto-disaccharides, Org. Lett., 3(9), 1323-1325, 2001.
39. Marco-Contelles, J, Martinez-Grau, A, Carbocycles from carbohydrates via free radical cyclizations: New synthetic approaches to glycomimetics, Chem. Soc. Rev., 27, 155-162, 1998.
40. Marco-Contelles, J, Alhambra, C, Martinez-Grau, A, Carbocycles from carbohydrates via free radical cyclizations: synthesis and manipulation of annulated furanoses, Synlett, 693-699, 1998.
41. Marco-Contelles, J, Pozuelo, C, Jimeno, M I, Martinez, L, Martinez-Grau, A, 6-Exo free-radical cyclization of acyclic carbohydrate intermediates-a new synthetic route to enantiomerically pure polyhydroxylated cyclohexane derivatives, J. Org. Chem., 57, 2625-2631, 1992.
42. Redlich, H, Sudau, W, Szardenings, A K, Vollerthun, R, 5-Carba analogs of sugars. 1. Radical cyclization of hept-1-enitols, Carbohydr. Res., 226, 57-78, 1992.
43. Gaudino, J J, Wilcox, C S, A general approach to carbocyclic sugar analogs-preparation of a carbocyclic analog of beta-D-fructofuranose, Carbohydr. Res., 206(2), 233-250, 1990.
44. Maudru, E, Singh, G, Wightman, R H, Radical cyclisation of carbohydrate alkynes: synthesis of highly functionalised cyclohexanes and carbasugars, Chem. Commun., 1505-1506, 1998.
45. Gomez, A M, Danelon, G O, Moreno, E, Valverde, S, Lopez, J C, A novel entry to 5a-carbahexopyranoses from carbohydrates based on a 6-exo-dig radical cyclization: synthesis of 5a-carbabeta-D-mannopyranose pentaacetate, Chem. Commun., 175-176, 1999.
46. Gomez, A M, Moreno, E, Valverde, S, Lopez, J C, Stereodivergent synthesis of carbasugars from Dmannose. Syntheses of 5a-carba-alpha-D-allose, beta-L-talose, and alpha-L-gulose pentaacetates, Synlett, 891-894, 2002.
47. Gomez, A M, Moreno, E, Valverde, S, Lopez, J C, A general stereodivergent strategy for the preparation of carbasugars. Syntheses of 5a-carba-alpha-D-glucose, alpha-D-galactose, and beta-Lgulose pentaacetates from D-mannose, Tetrahedron Lett., 43, 5559-5562, 2002.
48. Gomez, A M, Danelon, G O, Valverde, S, Lopez, J C, Regio-and stereocontrolled 6-endo-trig radical cyclization of vinyl radicals: a novel entry to carbasugars from carbohydrates, J. Org. Chem., 63, 9626-9627, 1998.
49. Mella, M, Panza, L, Ronchetti, F, Toma, L, 1,2-Dideoxy-3,4-5,7-bis-O-(1-methylethylidene)-D-gluco and D-galacto-hept-1-ynitols-synthesis and conformational studies, Tetrahedron, 44, 1673-1678, 1988.
50. Désiré, J, Prandi, J, A new synthesis of carbapentofuranoses from carbohydrates, Tetrahedron Lett., 38, 6189-6192, 1997.
51. Désiré, J, Prandi, J, The cobalt-catalyzed oxygenative radical route from hexopyranosides to carbapentofuranoses, Eur. J. Org. Chem., 3075-3084, 2000.
52. Callam, C S, Lowary, T L, Total synthesis of both methyl 4a-carba-D-arabinofuranosides, Org. Lett., 2, 167-169, 2000.
53. Callam, C S, Lowary, T L, Synthesis and conformational investigation of methyl 4a-carba-Darabinofuranosides, J. Org. Chem., 66, 8961-8972, 2001.
54. Seepersaud, M, Al-Abed, Y, Total synthesis of carba-D-fructofuranose via a novel metathesis reaction, Org. Lett., 1, 1463-1465, 1999.
55. Seepersaud, M, Kettunen, M, Abu-Surrah, A S, Repo, T, Voelter, W, Al-Abed, Y, Hydroformylation of cyclopentenes, novel strategy for total synthesis of carba-D-fructofuranose, Tetrahedron Lett., 43(10), 1793-1795, 2002.
56. Carpintero, M, Jaramillo, C, Fernandez-Mayoralas, A, Stereoselective synthesis of carba-and C-glycosyl analogs of fucopyranosides, Eur. J. Org. Chem., 1285-1296, 2000.
57. Dalko, P I, Sinaÿ, P, Recent advances in the conversion of carbohydrate furanosides and pyranosides into carbocycles, Angew. Chem. Int. Ed., 38, 773-777, 1999.
58. Ferrier, R J, Unsaturated carbohydrates 21. Carbocyclic ring-closure of a hex-5-enopyranoside derivative, J. Chem. Soc. Perkin. Trans., 1, 1455-1458, 1979.
59. Blattner, R, Ferrier, R J, Crystalline pseudo-alpha-D-glucopyranose, J. Chem. Soc. Chem. Comm., 1008-1009, 1987.
60. Barton, D H R, Gero, S D, Cleophax, J, Machado, A S, Quiclet-Sire, B, Synthetic methods for the preparation of D-pseudo-sugars and L-pseudo-sugars from D-glucose, J. Chem. Soc. Chem. Comm., 1184-1186, 1988.
61. Barton, D H R, Augy-Dorey, S, Camara, J, Dalko, P, Delaumény, J M, Géro, S D, Quiclet-Sire, B, Stütz, P, Synthetic methods for the preparation of basic D-pseudo-sugars and L-pseudo-sugars-synthesis of carbocyclic analogs of N-acetyl-muramyl-L-alanyl-D-isoglutamine (Mdp), Tetrahedron, 46, 215-230, 1990.
62. Das, S K, Mallet, J M, Sinaÿ, P, Novel carbocyclic ring closure of hex-5-enopyranosides, Angew. Chem. Int. Ed., 36, 493-496, 1997.
63. Sollogoub, M, Mallet, J M, Sinaÿ, P, Titanium (IV) promoted rearrangement of 6-deoxy-hex-5-enopyranosides into cyclohexanones, Tetrahedron Lett., 39, 3471-3472, 1998.
64. Sollogoub, M, Pearce, A J, Herault, A, Sinaÿ, P, Synthesis of carba-beta-D-and L-idopyranosides by rearrangement of unsaturated sugars, Tetrahedron-Asymmetry, 11, 283-294, 2000.
65. Pearce, A J, Sollogoub, M, Mallet, J M, Sinaÿ, P, Direct synthesis of pseudo-disaccharides by rearrangement of unsaturated disaccharides, Eur. J. Org. Chem., 9, 2103-2117, 1999.
66. Pearce, A J, Mallet, J M, Sinaÿ, P, One-step synthesis of disaccharide mimetics via tandem rearrangement of unsaturated disaccharides, Heterocycles, 52, 819-826, 2000.
67. Sollogoub, M, Mallet, J M, Sinaÿ, P, Carbocyclic ring closure of unsaturated S-, Se-, and C-aryl glycosides, Angew. Chem. Int. Ed., 39, 362-364, 2000.
68. Sudha, A V R L, Nagarajan, M, Carbohydrates to carbocycles: an expedient synthesis of pseudosugars, Chem. Commun., 925-926, 1998.