The stereodirecting effect of the glycosyl C5-carboxylate ester: stereoselective synthesis of β-mannuronic acid alginates

…, HS Overkleeft, GA van der Marel

文献索引：Codee, Jeroen D. C.; Stubba, Bas; Schiattarella, Marialuisa; Overkleeft, Herman S.; Van Boeckel, Constant A. A.; Van Boom, Jacques H.; Van Der Marel, Gijsbert A. Journal of the American Chemical Society, 2005 ,  vol. 127,  # 11  p. 3767 - 3773

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被引用次数: 54

摘要

Glycosylations of mannuronate ester donors proceed highly selectively to produce the 1, 2- cis-linked products. We here forward a mechanistic rationale for this counterintuitive selectivity, based on the remote stereodirecting effect of the C5-carboxylate ester, which has been demonstrated using pyranosyl uronate ester devoid of ring substituents other than the C5-carboxylate ester. It is postulated that the C5-carboxylate ester prefers to occupy an ...