ISSN:
0947-3440
Keywords:
C-Glycosylation
;
C-Glycosyl arenes
;
Trichloroacetimidate method
;
N-Tetrachlorophthaloyl, protection and deprotection
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
The N-tetrachlorophthalimido-protected glucosamine donor 2 reacts with electron-rich phenol ethers 3a-c to afford aryl C-glycosides 4a-c. The N-tetrachlorophthaloyl group could be readily removed by sodium borohydride treatment and then phthalide formation or by treatment with ethylenediamine, respectively. The resulting product was subjected to reaction with acetic anhydride in pyridine to afford N,O-acetylated compounds 5a-c. After treatment with enthylenediamine also the N,O-unprotected compounds could be obtained as shown for 6c.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199619961019
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