Abstract
Synthetic photochemical applications to carbohydrates are described by photosubstitution, photoaddition, photoizomerisation, photoreduction, and photoxidation reactions. The use of photoremovable protecting groups in osidic syntheses is also evoked.
The recent development of such radical reactions using photoinitiators is mainly due to their regio and stereoselectivities interpreted in terms of stabilized conformations of carbohydrate radicals by stereoelectronic factors. The preferential α-attack of anomeric radicals is a well documented example of such transformations.
Some new methodologies using single electron transfer reactions are also indicated in this review.
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8 References
Binkley RW (1981) Adv. Carb. Chem. Biochem. 28: 105
Viehe HG, Janousek Z, Merenyi R (1985) Acc. Chem. Res. 18: 148
Mc Kelvey RD, Iwamura H (1985) J. Org. Chem. 50: 402
Deslongchamps P (1983) Stereoelectronic effects in organic chemistry, Pergamon, Oxford
Giese B (1986) Radicals in organic synthesis: formation of carbon-carbon bond, Pergamon, Oxford
Descotes G (1982) Bull. Soc. Chim. Belges, 91: 973
Box VGS (1984) Heterocycles, 22: 891
Somsak L, Batta G, Farkas I (1983) Carbohydr. Res., 124: 43
Praly JP, Descotes G (1987) Tetrahedron Lett., 28: 1405
Lichtenthaler FW, Frieder W, Jarglis P (1982) Angew. Chem., 948: 643
Lichtenthaler F, Jarglis P, Hempe W (1983) Liebigs Ann. Chem. 1959
Lichtenthaler FW, Kaji E, Weprek S (1985) J. Org. Chem., 50: 3505
Lichtenthaler FW, Kaji E (1985) Liebigs Ann. Chem. 1659
Collins PM, Manro A, Oppara Mottah C, Ali MH (1988) J. Chem. Soc. Chem. Commun. 272
Praly JP, Descotes G (1982) Tetrahedron Lett., 23: 849
Praly JP, Descotes G, Grenier-Loustalot MF, Metras F (1984) Carbohydr. Res., 128:21
Wright DE (1979) Tetrahedron 35: 1207
Praly JP (1983) Tetrahedron Lett., 24: 3075
Somsak L, Butta G, Farkas I (1986) Tetrahedron Lett., 27: 5877
Giese B, Dupuis J (1983) Angew. Chem. Int. Ed. Eng., 22: 622
Giese B, Dupuis J, Nix M (1987) Org. Synth., 65: 236
Adlington RM, Baldwin JE, Basak A, Kozyrod RP J. Chem. Soc. Chem. Commun. 1983: 944
Korth HE, Sustmann R, Dupuis J, Giese B (1986) J. Chem. Soc. Perkin Trans 11: 1452
Giese B, Witzel T (1986) Angew. Chem. Int. Ed. Engl., 25: 450
Aebischer B, Meuwly R, Vasella A (1984) Helv. Chim. Acta., 67: 2236
Hashimoto S, Kurimoto I, Fujii Y, Noyori F (1985) J. Am. Chem. Soc., 107: 1427
Ferrier RJ, Furneaux RH J. Chem. Soc. Perkin 1. 1977: 1996
Ferrier RJ, Tyler PC J. Chem. Soc. Perkin 1, 1980: 2767
Blattner R, Ferrier RJ J. Chem. Soc. Perkin 1, 1980: 1523
Ferrier RJ, Furneaux RH (1980) Aust. J. Chem., 33: 1025
Chiba T, Sinay P (1984) Carbohydr. Res., 151: 379
Blattner R, Ferrier RJ (1986) Carbohydr. Res., 150: 151
Ferrier RJ, Haines SR J. Chem. Soc. Perkin I, 1984: 1675
Ferrier RJ, Haines SR, Gainsford GJ, Gabe EJ: J. Chem. Soc. Perkin I, 1984: 1683
Ferrier RJ: J. Chem. Soc. Perkin I, 1985: 2413
Ferrier RJ: J. Chem. Soc. Perkin I, 1979: 1455
Blattner R, Ferrier RJ, Prasit P: J. Chem. Soc. Perkin I, 1980: 944
Ohrui H, Horiki H, Kishi H, Meguru H (1983) Agric. Biol. Chem., 47: 1101
Ohrui H, Yoshihiro N, Hiroshi M (1984) Agric. Biol. Chem., 48: 1049
Ohrui H, Tsutami M, Hiroshi M (1984) Agric. Biol. Chem. 48: 1825
Giese B, Gonzales-Gomez JA, Witzel T (1984) Angew. Chem., 96: 51
Giese B, Roninger KG (1984) Tetrahedron Lett., 25: 2743
Keck GE, Kachensky DF, Enholm EJ (1984) J. Org. Chem., 49: 1462
Keck GE, Yates JB (1982) J. Am. Chem. Soc., 104: 5829
Fitzsimmons BJ, Fraser-Reid B (1979) J. Am. Chem. Soc., 101: 6123
Bonjouklian R, Ganem B (1979) Carbohydr. Res., 76: 245
Kozlowska-Gramsz E, Descotes G (1982) Canad. J. Chem., 60: 558
Lessard J, Mondon M, Touchard D (1981) Canad. J. Chem., 59: 431
Igarashi K, Honma T (1970) J. Org. Chem., 35: 606
Fitzsimmons BJ, Leblanc Y, Rokach J (1987) J. Am. Chem. Soc., 109: 285
Fetizon M, Ducdokhac Nguyen Dinh Tho (1986) Tetrahedron Lett., 26: 1777
Matsui T, Morooka T, Akayama MN (1987) Bull. Chem. Soc. Japan., 60: 417
Fraser-Reid B, Anderson RC (1980) Fortschr. Chem. Org. Naturst., 39: 1
Araki Y, Senna K, Matsuura K, Ishido Y (1978) Carbohydr. Res., 60: 389
Jarosz S, Zamojski A (1983) Pol. J. Chem., 57: 57; (1982) Tetrahedron, 83: 1453
Araki Y, Nagasawa J, Ishido Y: J. Chem. Soc. Perkin I, 1981: 12
Bovin NV, Zurabyan SE, Khorlin AY (1981) Carbohydr. Res. 98: 25
Bovin NV, Zurabyan SE, Khorlin AY (1983) J. Carb. Chem. 2: 249
Chmielewski M, Bemiller JN, Cerretti D (1981) J. Org. Chem., 46: 3903
Rosenthal A, Chow J (1980) J. Carbohydr. Nucleosides, Nucleotides, 7: 77
Araki Y, Nishiyama K, Matsuura K (1978) Carbohydr. Res. 63: 288
Araki Y, Nishiyama K, Senna K, Matsuura K, Ishido Y (1978) Carbohydr. Res. 64: 119
Kozlowska-Gramsz E, Descotes G (1982) Tetrahedron Lett. 23: 1585
Fraser-Reid B, Holder NL, Hicks DR, Walker DL (1977) Can. J. Chem., 55: 3978
Benko Z, Fraser-Reid B, Mariano PS, Beckwith ALJ (1988) J. Org. Chem. 53: 2066
Sakakibara T, Nakagawa T (1987) Carbohydr. Res., 163: 239
Holder NL (1982) Chem. Rev. 82: 287
Hicks DR, Anderson RC, Fraser-Reid B Synth. Commun. 1976: 417
Fraser-Reid B, Walker DR (1980) Can. J. Chem., 58: 2694
Collins PM, Iyer R, Travis AS (1978) J. Chem. Res., 5: 446
Heyns K, Neste HP, Thiem J (1981) Chem. Ber., 114: 891
Collins PM, Gupta R, Travis AS J. Chem. Soc. Perkin I 1980: 277
Collins PM, Farnia F, Munasinghe VRN, Oparaech NN, Siavoshy F. J. Chem. Soc. Chem. Commun. 1985: 1038
Collins PM, Farnia F, Travis AS J. Chem. Res., (S) 1979: 266
Remy G, Cottier L, Descotes G (1980) Can. J. Chem., 58: 2660
Remy G, Cottier L, Descotes G (1982) J. Carbohydr. Res. 1: 37
Remy G, Descotes G (1983) J. Carbohydr. Res. 2: 159
Remy G, Cottier L, Descotes G (1983) Can. J. Chem. 61: 434
Bernasconi C, Cottier L, Descotes G, Praly JP (1983) Carbohydr. Res. 115: 105
Remy G, Cottier L, Descotes G, Faure R. Loiseleur H (1980) Acta Cryst. B36: 873
Remy G, Cottier L, Descotes G, Faure R, Loiseleur H (1982) Cryst. Struct. Commun. 11: 235
Cottier L, Remy G, Descotes G Synthesis 1979: 711
Pete JP, Portella C, Monneret C, Florent JC, Khuong Huu Q Synthesis 1977: 774
Portella C, Deshayes H, Pete JP, Scholler D (1984) Tetrahedron. 40: 3635
Portella C, Pete JP (1985) Tetrahedron Lett. 26: 211
Pete JP, Portella C, Scholler D (1984) J. Photochem., 27: 128
Pete JP, Portella C: Bull. Soc. Chim. Fr. 1985: 195 and references herein
Collins PM, Ranjit V, Munasinghe Z: J. Chem. Soc., Chem. Commun., 1977: 1927
Hartwig W (1983) Tetrahedron 39: 2609
Klausener A, Muller E, Runsink J, Scharf HD (1985) Carbohydr. Res., 116: 295
Dornhagen J, Scharf HD J. Carbohydr. Chem. 5: 115 (1986)
Dornhagen J, Klausener A, Runsink J, Scharf HD Liebigs Ann. Chem. 1985: 1838
Saito I, Ikehira H, Kasatani R, Watanabe M, Matsuura T (1986) J. Am. Chem. Soc., 108: 3115
Kishi T, Tsuchiya T, Umezawa S (1979) Bull. Chem. Soc. Japan, 52: 3015
Tsuchiya T, Nakamura F, Umezawa S (1979) Tetrahedron Lett., 30: 2805
Bell RH, Horton D, Williams DM, Winter-Mihaly E (1977) Carbohydr. Res. 58: 109
Descotes G, Faure A, Kryczka B, Bouchu MN (1979) Bull. Soc. Sci. Pol., 27: 173
Binkley RW, Bankaitis D (1982) J. Carbohydr. Chem., 1: 1
Roth RC, Binkley RW (1985) J. Org. Chem. 50: 690
Binkley RW, Fan JC (1982) J. Carbohydr. Chem. 1: 213
Binkley RW (1977) J. Org. Chem. 42: 1216
Binkley RW, Hehemann DG, Binkley WB (1978) J. Org. Chem., 43: 2573
Binkley RW (1985) J. Carbohydr. Chem. 4: 227
Binkley RW (1980) Methods Carbohydr. Chem. 8: 321
Dendruver L, Holzapfel CW, Vandick MS, Kruger GJ (1987) Carbohydr. Res., 161: 65
Bernasconi C, Cottier L, Descotes G, Remy G (1979) Bull. Soc. Chim. Fr. 1979: 332
Sato T, Takahashi K, Ichikawa S Chemistry Lett. 1983: 1589
Araki K, Sakuma M, Shiraishi S Chemistry Lett. 1983: 665
Ichikawa S, Sato T (1986) Tetrahedron Lett., 27: 45
Pillai VNR: Synthesis 1980: 1
Binkley RV, Goewey GS, Johnston JC (1984) J. Org. Chem. 49: 992
Collins PM, Munasinghe V J. Chem. Soc. Perkin I 1983: 921
Collins PM, Eder H: J. Chem. Soc. Perkin I 1983: 927
Collins PM, Munasinghe V J. Chem. Soc. Perkin I, 1983: 1879
Baines FC, Collins PM, Farnia F (1985) Carbohydr. Res. 136: 27
Ohtsuka E, Tanaka S, Ikehara M: Synthesis 1977: 453
Hayes JA, Brunder MJ, Gilham PT, Gough GR (1985) Tetrahedron Lett., 26: 2407
Rubinstein M, Amit B, Patchornik A: Tetrahedron Lett. 1975: 1445
Hanessian S, Masse R (1977) Carbohydr. Res., 54: 142
Binkley RW, Koholic DJ (1984) J. Carbohydr. Chem. 3: 85
Masnovi J, Koholic DJ, Berki RJ, Binkley RW (1987) J. Am. Chem. Soc. 109: 2851
Flechtner FW, Pohlid H (1984) J. Carbohydr. Chem. 3: 107
Ramamurthy V (1986) Tetrahedron 42: 5753
Gnewuch T, Sosnovsky G (1986) Chem. Rev. 86: 203
Myers RW, Chuan Lee Y (1986) Carbohydr. Res. 152: 143
Lehmann J, Thieme R Liebigs Ann. Chem. 1986: 525
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Descotes, G. (1990). Synthetic saccharide photochemistry. In: Carbohydrate Chemistry. Topics in Current Chemistry, vol 154. Springer, Berlin, Heidelberg. https://doi.org/10.1007/BFb0111559
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DOI: https://doi.org/10.1007/BFb0111559
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