Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 70, Issue 22, Pages 9059-9062Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo051390g
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Funding
- BBSRC [BBS/E/J/000C0618] Funding Source: UKRI
- Engineering and Physical Sciences Research Council [GR/S64134/01] Funding Source: researchfish
- Biotechnology and Biological Sciences Research Council [BBS/E/J/000C0618] Funding Source: Medline
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[GRAPHIC] Activation of ester-protected glycosyl trichloroacetimidate donors by perchloric acid immobilized on silica afforded 1,2-trans disaccharides in 60-90% yields. Applying this approach to one-pot sequential glycosylation resulted in efficient syntheses of the N-linked glycan trimannoside and Lex and LeA trisaccharides in very good yield (76%, 62%, and 59% yields, respectively). Solution phase reactions were also translated to a solid phase format; priming the top of a standard silica chromatography column with perchloric acid immobilized on silica facilitated on-column glycosylation with subsequent in situ purification of products. Coupling yields from this approach were comparable to those obtained from the corresponding solution-phase disaccharide couplings. A series of glycosylated amino acids were also synthesized in high yield with use of the on-column approach.
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