A new method for the formation of the α-glycoside bond of sialyl conjugates based on long-range participation

Tetrahedron Letters

Volumn 38, Issue 47, 1997, Pages 8223-8226

  Takahashi, Takashi ^a   Tsukamoto, Hirokazu ^a   Yamada, Haruo ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; N ACETYLNEURAMINIC ACID; SIALIC ACID DERIVATIVE;

ARTICLE; CELL ADHESION; CELL DIFFERENTIATION; GLYCOSYLATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0030726264     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10200-3     Document Type: Article

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13. Application of PM3 calculations to the α-and β-sulfonium intermediates (all hydroxy groups and side chain at C5 in sialic acid were replaced by hydrogens for simplicity of calculations ) revealed that the energy of β-sulfonium intermediate 14A was calculated to be 1.2 kcal/mol more stable than that of αsulfonium intermediate 14B. Chemical equations presented.
14. 11)) in 61% overall yield.
15. 8,9=5.6Hz, H-8).
16. 8,9=7.6Hz, H-8).
17. 7,8=7.8Hz, H-7), 5.41 (ddd, 1H, H-8).
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