A novel intramolecular decarboxylative glycosylation via mixed carbonate

Tetrahedron Letters

Volumn 37, Issue 13, 1996, Pages 2267-2270

  Iimori, Takamasa ^a   Shibazaki, Takafumi ^a   Ikegami, Shiro ^a  

^a TEIKYO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATE DERIVATIVE;

ARTICLE; CARBOHYDRATE SYNTHESIS; GLYCOSYLATION; REACTION ANALYSIS;

EID: 0029930476     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00272-9     Document Type: Article

References (15)

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3. Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1986, 25, 212.
4. (a) Schmidt, R. R.; Reichrath, M. Angew. Chem., Int. Ed. Engl. 1979, 18, 466.
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6. (a) Staab, H. A.; Mannschreck, A. Chem. Ber. 1962, 95, 1284.
7. Imidazolide has been used for the formation of 2-(trimethylsilyl)ethyl carbonate: (b) Roush, W. R.; Blizzard, T. A. J. Org. Chem. 1984, 49, 4332.
8. Nitrophenyl carbonates 2 or imidazolides 3 were obtained by reactions of corresponding alcohols with commercially available 4-nitrophenyl chloroformate with triethylamine or carbonyldiimidazole respectively.
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12. (b) Ishido, Y.; Inaba, S.; Matsuno, A.; Yoshino, T.; Umezawa, H. J. Chem. Soc., Perkin Trans. 1 1977, 1382.
13. Narasaka has reported similar solvent effects on enantioselectivity in asymmetric pericyclic reactions: (a) Narasaka, K.; Inoue, M.; Yamada, T.; Sugimori, J.; Iwasawa, N. Chem. Lett. 1987, 2409.
14. (b) Narasaka, K.; Hayashi, Y.; Shimada, S. Chem. Lett. 1988, 1609.
15. 7 We are now investigating β-selective carbonate formation of acyl protected sugars and their decarboxylative glycosylation.