Stereoselective synthesis of α-C-(alkynyl)-glycosides via ring-opening of α-1,2-anhydrosugars

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6251-6254

  Leeuwenburgh, Michiel A ^a   Timmers, Cornelis M ^a   Van Der Marel, Gijsbert A ^a   Van Boom, Jacques H ^a   Mallet, Jean Maurice ^b   Sinaÿ, Pierre G ^b  

^a LEIDEN UNIVERSITY   (Netherlands)

^b ECOLE NORMALE SUPÉRIEURE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE; GLYCOSIDE;

ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030802867     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01381-6     Document Type: Article

References (15)

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2. C.M. Timmers, M. Dekker, R.C. Buijsman, G.A. van der Marel, B. Ethell, G. Anderson, B. Burchell, G.J. Mulder, J.H. van Boom, Bioorg. Med. Chem. Lett., in press; C.M. Timmers, Ph.D. Thesis, Leiden 1997.
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6. 2-mediated condensation of epoxide 1 with primary alcohols affords a mixture of α and β anomers.
7. 3 Ac).
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12. For previous C-isomaltoside syntheses, see: P.G. Goekjian, T-C. Wu, H-Y. Kang, Y. Kishi, J. Org. Chem. 1991, 56, 6422; O.R. Martin, F. Xie, R. Kakarla, R. Benhamza, Synlett, 1993, 165; D. Mazéas, T. Skrydstrup, O. Doumiex, J-M. Beaux, Angew. Chem. Int. Ed. Engl., 1994, 33, 1383.
13. For previous C-isomaltoside syntheses, see: P.G. Goekjian, T-C. Wu, H-Y. Kang, Y. Kishi, J. Org. Chem. 1991, 56, 6422; O.R. Martin, F. Xie, R. Kakarla, R. Benhamza, Synlett, 1993, 165; D. Mazéas, T. Skrydstrup, O. Doumiex, J-M. Beaux, Angew. Chem. Int. Ed. Engl., 1994, 33, 1383.
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