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Synlett 1998; 1998(1): 84-86
DOI: 10.1055/s-1998-1575
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Mild but Efficient Methods for Stereoselective Glycosylation with Thioglycosides: Activation by [N-Phenylselenophthalimide-Mg(ClO4)2] and [PhIO-Mg(ClO4)2]

Koichi Fukase* , Yoshihiko Nakai, Takeshi Kanoh, Shoichi Kusumoto
  • *Department of Chemistry, Graduate School of Science, Osaka University, Toyonaka, Osaka 560, Japan; Fax +81 6 8 50 54 19; E-mail: koichi@chem.sci.osaka-u.ac.jp
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Publication History

Publication Date:
31 December 2000 (online)

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Combinations of N-phenylselenophthalimide (N-PSP) or iodosobenzene (PhIO) with Mg(ClO4)2 effectively promote glycosylation with thioglycosides under mild conditions. A 2,2,2-trichloroethoxycarbonyl group or trityl protecting group at the 6-position increased α-selectivity on glycosylation with 2-O-benzylated donors.

glycosylation - thioglycoside - N-phenylselenophthalimide - iodosobenzene

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