Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: Remarkable 1,2-trans stereoselectivity

Tetrahedron Letters

Volumn 44, Issue 50, 2003, Pages 8971-8974

  Girard, Nicolas ^a   Rousseau, Cyril ^a   Martin, Olivier R ^a  

^a CNRS   (France)

Author keywords

C aryl glycosides; C glycosylation

Indexed keywords

ALCOHOL DERIVATIVE; PERCHLORATE; PYRANOSIDE;

ARTICLE; CHROMATOGRAPHY; EPIMERIZATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0242626855     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.10.006     Document Type: Article

References (30)

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15. 3,4=10.2 Hz, H-3), 5.39 (t, 1H, J=9.8 Hz, H-4), 6.34 (s, 1H, H-6′).
16. For the related epimerization of an α-C-mannosylated phloroacetophenone derivative, see: Kumazawa T., Sato S., Matsuba S., Onodera J.-I. Carbohydr. Res. 332:2001;103-108.
17. Compound 5 undergoes rapid 2-O-debenzylation in the presence of hard, oxophilic Lewis acids.
18. The reaction gave iodinated starting material as the major product, an indication that the reaction of the aromatic residue with IDCP is faster than that of the pentenyl group. Iodination took place at C-2 of the 3,5-dimethoxybenzyl group. Isolated yields: iodinated starting material: 37%, 11: 18%, 12: 5%.
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20. Glycosyl perchlorates have been reported. See: (a) Zhdanov, Y. A.; Korol'chenko, G. A.; Dorofeenko, G. N.; Zhungietu, G. I. Dokl. Akad. Nauk SSSR 1964, 154, 861-863; (b) Igarashi, K.; Honma, T.; Irisawa, J. Carbohydr. Res. 1970, 15, 329-337. We thank a referee for suggesting the possible involvement of a glycosyl perchlorate.
21. Glycosyl perchlorates have been reported. See: (a) Zhdanov, Y. A.; Korol'chenko, G. A.; Dorofeenko, G. N.; Zhungietu, G. I. Dokl. Akad. Nauk SSSR 1964, 154, 861-863; (b) Igarashi, K.; Honma, T.; Irisawa, J. Carbohydr. Res. 1970, 15, 329-337. We thank a referee for suggesting the possible involvement of a glycosyl perchlorate.
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23. 6, attributions verified by H,C-correlation): δ 20.8. 21.0 (Ac), 56.1, 61.2, 62.2 (3 OMe), 60.2 (C-6), 63.8 (C-1), 67.8 (C-3), 69.3 (C-4), 74.9 (C-2), 75.6 (C-5), 110.7 (C-6′), 120.5 (C-2′), 127.4 (C-1′), 149.9, 152.8, 154.8 (C-3′,4′,5′), 163.9 (C-7), 169.4, 169.6 (MeCOO).
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25. 11 The product was contaminated by an unseparable by-product; identifiable NMR signals appear to indicate that this product could be a small amount of the cis-epimer of 16.
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28. α-C-Aryl glycosides have been obtained under certain conditions. See for example Ref. 11 and (a) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296; (b) Cai, M.-S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129; (c) Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831.
29. α-C-Aryl glycosides have been obtained under certain conditions. See for example Ref. 11 and (a) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296; (b) Cai, M.-S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129; (c) Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831.
30. α-C-Aryl glycosides have been obtained under certain conditions. See for example Ref. 11 and (a) Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289-4296; (b) Cai, M.-S.; Qiu, D.-X. Carbohydr. Res. 1989, 191, 125-129; (c) Schmidt, R. R.; Effenberger, G. Liebigs Ann. Chem. 1987, 825-831.