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Volumn 5, Issue 5, 2010, Pages 1152-1162

Rate-dependent inverse-addition β-selective mannosylation and contiguous sequential glycosylation involving β-mannosidic bond formation

Author keywords

selectivity; Glycosylation; Inverse addition; Mannosylation; Oligosaccharides

Indexed keywords

ADDITION RATE; BOND FORMATION; GLYCOSYLATIONS; N-LINKED; RATE DEPENDENT; REPEATING UNIT; SYNTHETIC UTILITY; THIOGLYCOSIDES;

EID: 77951798727     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.200900765     Document Type: Article
Times cited : (15)

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    • N-(b-Mannopyranosyl) trichloroacetamide 5 was isolated and the anomeric configuration was evidenced by the 13C NMR spectroscopic chemical shift at d=79.4 ppm and the 1JCH coupling constant of 161 Hz (see the Experimental Section).
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    • This explanantion was suggested by one of the referees in the revision of this manuscript, whereas in our perspective, we do not exclude other possible causes unless further experimental evidence is obtained
    • This explanantion was suggested by one of the referees in the revision of this manuscript, whereas in our perspective, we do not exclude other possible causes unless further experimental evidence is obtained.
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    • Syntheses of 13, 14, 16, 17, 23, 24, and 25 were detailed in the Supporting Information. Since synthesis of 15 and 16 employed the same route, only the synthesis of 16 was described in the Supporting Information. For the synthesis of 16: a) J. Gildersleeve, R. A. Pascal, D. Kahn, J. Am. Chem. Soc. 1998, 120, 5961-5969;
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    • Synthesis of 28 was described in the Supporting Information
    • Synthesis of 28 was described in the Supporting Information.
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