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Original Articles

The Tmsotf-Promoted “One Pot” β-Glycosidations of Peracetylated Chitobiose

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Pages 297-302 | Received 08 Aug 1995, Accepted 11 Dec 1995, Published online: 22 Aug 2006

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  • Peracetylated chitobiose oxazoline was prepared by treatment of peracetylated chitobiose 1 with TMSOTf, as described by H. Kuzuhara et al.8. After the reaction was completed, the mixture was poured into ice-cold aqueous sodium hydrogen-carbonate, extracted with CH2Cl2. The CH2Cl2 layer was washed with water, dried, and concentrated. The residue was chromatographed on silica gel with 50:1(v/v) CH2Cl2–MeOH as the eluent, yield 95%.
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