Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 84, Issue 23, Pages 15052-15062Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.9b01492
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Funding
- National Science Foundation (NSF) [1465003]
- National Institute of General Medical Sciences [U01GM120673]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1465003] Funding Source: National Science Foundation
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A novel 8-O-picoloylated sialyl donor has been developed, and the performance of various picoloylated sialyl donors in glycosylations with primary glycosyl acceptors has been evaluated. 8-O-Picoloyl and 4,9-di-O-picoloyl sialyl donors produced moderate to excellent yields of disaccharides with complete alpha-stereoselectivities. Synergistic effects between picoloyl and the accompanying O-protecting groups (benzoyl vs acetyl) were evaluated, as well as the effects of triflic acid concentration on the 8-O-picoloyl donor. H-1 NMR analysis was also carried out to assess differences in the hydrogen-bonding
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