Carbohydrate Homologation by the Use of 2-(Trimethylsilyl)thiazole. Preparative Scale Synthesis of Rare Sugars: L-Gulose, L-Idose, and the Disaccharide Subunit of Bleomycin A2

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6261-6267

  Dondoni, Alessandro ^a   Marra, Alberto ^a   Massi, Alessandro ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000373613     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970601h     Document Type: Article

References (56)

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17. For overviews, see: (a) Dondoni, A. Pure Appl. Chem. 1990, 62, 643. (b) Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; p 377. Dondoni, A. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, and VCH: Weinheim, 1992; p 105. Dondoni, A.; Marra, A. In Preparative Carbohydrate Chemistry, Hanessian, S., Ed., Marcel Dekker: New York, 1997; p 173.
18. For overviews, see: (a) Dondoni, A. Pure Appl. Chem. 1990, 62, 643. (b) Dondoni, A. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; p 377. Dondoni, A. In New Aspects of Organic Chemistry II; Yoshida, Z., Ohshiro, Y., Eds.; Kodansha: Tokyo, and VCH: Weinheim, 1992; p 105. Dondoni, A.; Marra, A. In Preparative Carbohydrate Chemistry, Hanessian, S., Ed., Marcel Dekker: New York, 1997; p 173.
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35. 4NF induces the desilylation of the O-silyl ether adduct into alcohol. A mechanistic explanation of this peculiar organosilane addition reaction has been provided, see: (a) Dondoni, A.; Douglas, A. W.; Shinkai, I. J. Org. Chem. 1993, 58, 3196. (b) Wu, Y.-D.; Lee, J. K.; Houk, K. N.; Dondoni, A. J. Org. Chem. 1996, 61, 1922.
36. 4NF induces the desilylation of the O-silyl ether adduct into alcohol. A mechanistic explanation of this peculiar organosilane addition reaction has been provided, see: (a) Dondoni, A.; Douglas, A. W.; Shinkai, I. J. Org. Chem. 1993, 58, 3196. (b) Wu, Y.-D.; Lee, J. K.; Houk, K. N.; Dondoni, A. J. Org. Chem. 1996, 61, 1922.
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48. Crude 21 upon flash chromatography over silica gel gave a complex mixture of products arising from intramolecular transesterification reactions.
49. Our product contained 5% of the α-anomer at the L-gulose moiety. Since the acceptor 21 was used as a 80:20 mixture of β-L and α-L anomers, this result indicates that considerable anomerization of the L-gulose unit took place during the TMSOTf-promoted glycosylation.
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