Synthesis of a sialyl Lewis x mimic with fixed carboxylic acid group: Chemical approach toward the elucidation of the bioactive conformation of sialyl Lewis x

Journal of Organic Chemistry

Volumn 61, Issue 2, 1996, Pages 514-524

  Thoma, Gebhard ^a   Schwarzenbach, Franz ^a   Duthaler, Rudolf O ^a  

^a CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIAL LEUKOCYTE ADHESION MOLECULE 1; OLIGOSACCHARIDE;

ARTICLE; BLOOD GROUP LEWIS SYSTEM; DRUG PROTEIN BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE;

EID: 0030043567     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951067l     Document Type: Article

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41. A disaccharide such as 4 (R = Bn, compound 26 in Scheme 4) was generously provided by Dr. N. Cooke, CIBA-Basel. The synthesis is not covered in the Experimental Section and will be published elsewhere.
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45. The synthesis of 28 and 29 is not covered in the Experimental Section.
46. In an earlier attempt toward a bicyclic glycosyl donor such as 3 we had prepared advanced intermediate 46. Unfortunately, we were unable to remove the axial anomeric benzyl group.
47. Compound 30 was generously provided by Dr. George Papandreou. The synthesis of 30 is not covered in the Experimental Section and will be published elsewhere.