Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 10, Pages 2138-2142Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500186
Keywords
Iodine; Phenyliodine bis(trifluoroacetate); Glycosylation; Thioglycosides
Categories
Funding
- Japan Society for the Promotion of Science (JSPS)
- Ministry of Education, Culture, Sports, Science and Technology (MEXT)
- JSPS
- Grants-in-Aid for Scientific Research [26460022, 25860017] Funding Source: KAKEN
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A combination of phenyliodine bis(trifluoroacetate) (PIFA) and trifluoromethanesulfonic acid was found to be an effective activator for the glycosylation reaction, of which the glycosyl donor was p-(octyloxy)phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-D-glucopyranoside or p-(octyloxy)phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-D-galactopyranoside. The reaction proceeded with good yields when naturally occurring and derived alkanols, such as cholestanol, (-)-menthol, 1- and 2-adamantanols and nor-kauranol, were employed as acceptor substrates. Interestingly, the glycosylation reaction of sterically hindered terpenoid alcohols, such as (-)- and (+)-borneols and (+)-fenchyl alcohol, with p-(octyloxy)phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-D-glucopyranoside afforded the desired -glycoside in quantitative yield. Moreover, the present reaction was useful to synthesize disaccharides of which the non-reducing end was composed of a D-glucosamine or D-galactosamine unit.
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