Regioselective synthesis of 1I,1II,5I,5II,6I,6I,6II,6II-2H8-cellobiose |
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Authors: | Zhang Fuyi Vasella Andrea |
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Institution: | Laboratorium für Organische Chemie, ETH Zürich, Switzerland. |
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Abstract: | Partially deuteriated 1,5,6,6-(2)H(4)-d-glucose and 1(I),1(II),5(I),5(II),6(I),6(I),6(II),6(II)-(2)H(8)-d-cellobiose were synthesized in high yields and on a large scale from d-glucose. (2)H enrichment at C-5 and C-6 of each glucopyranosyl unit in excess of 85% and 90%, respectively, was realized by (1)H-(2)H exchange in (2)H(2)O containing deuteriated Raney Ni. Nucleophilic addition of LiAlD(4) to 5,6,6-(2)H(3)-2,3,4,6-tetra-O-benzyl-d-gluconolactone led to a 98% (2)H enrichment at C-1. Deuteriated cellobiose is of interest as building block for the synthesis of a model compound of cellulose I. |
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Keywords: | 1 5 6 d-Glucose" target="_blank">6-2H4-d-Glucose 1I 1II 5I 5II 6I 6I 6II 6II-2H8-cellobiose 2H enrichment Gluconolactone Glycosidation Trichloroacetimidate Cellulose I |
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