Studies on 1-Deoxynojirimycin-Containing Glycans: Synthesis of Novel Disaccharides Related to Lactose, Lactosamine, and Chitobiose
- 1 July 1992
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 11 (5) , 627-644
- https://doi.org/10.1080/07328309208016153
Abstract
Suitably protected 1-deoxynojirimycin (l, 5-dideoxy-l, 5-imino-D-glucitol; DNJ) and its 2-acetamido derivative, i.e., 2, 3, 6-tri-O-benzyl-.N-benzyloxycarbonyl-l, 5-dideoxy-1, 5-imino-D-glucitol (6) and 2-acetamido-3, 6-di-O-benzyl-N-benzyloxycarbonyl-1, 2, 5-trideoxy-l, 5-imino-D-glucitol (14) were each coupled with methyl 2, 3, 4, 6-tetra-O-acetyl-1-thio-β-D-galactopyranoside (15) in the presence of dimethyl(methylthio)-sulfonium triflate (DMTST) as a promoter, to give 16 and 18, which were converted to the novel disaccharides (20, 21) related to lactose and lactosamine. Coupling of 14with methyl 3, 4, 6-tri-O-acetyl-2-deoxy-2-phthalimido-l-thio-β-D-glucopyranoside (22) gave achitobiose analog (25). O-(β-D-Galactopyranosyl)-(l→3)-DNJ derivatives (38, 39) and O-(β-D-glucopyranosyl)-(l→3)-DNJ (45) were also synthesized. Conformational analysis of a variety of DNJ derivatives, based on the 1H NMR data, is also discussed.Keywords
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